[ CAS No. 79349-82-9 ] {[proInfo.proName]}

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Quality Control of [ 79349-82-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 79349-82-9 ]

SDS Specification

Alternatived Products of [ 79349-82-9 ]

Product Details of [ 79349-82-9 ]

CAS No. :	79349-82-9	MDL No. :	MFCD07782149
Formula :	C₉H₁₀N₂O₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GQLGFBRMCCVQLU-SVGQVSJJSA-N
M.W :	226.25	Pubchem ID :	7280824
Synonyms :

Calculated chemistry of [ 79349-82-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.33
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	59.28
TPSA :	108.93 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-9.65 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.78
Log Po/w (XLOGP3) :	-2.78
Log Po/w (WLOGP) :	-0.63
Log Po/w (MLOGP) :	0.21
Log Po/w (SILICOS-IT) :	-0.33
Consensus Log Po/w :	-0.55

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	0.64
Solubility :	989.0 mg/ml ; 4.37 mol/l
Class :	Highly soluble
Log S (Ali) :	1.05
Solubility :	2520.0 mg/ml ; 11.1 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	0.15
Solubility :	317.0 mg/ml ; 1.4 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.08

Safety of [ 79349-82-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 79349-82-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 79349-82-9 ]
Downstream synthetic route of [ 79349-82-9 ]

[ 79349-82-9 ] Synthesis Path-Upstream 1~3

1
[ 104797-47-9 ]
[ 79349-82-9 ]
[ 91832-40-5 ]

Yield	Reaction Conditions	Operation in experiment
88.6%	Stage #1: With triethylamine In tetrahydrofuran at 20 - 23℃; for 5 h; Stage #2: With hydrogenchloride; methoxybenzene In tetrahydrofuran; dichloromethane at -25 - -20℃; for 1.5 h;	In a dry reaction flask, add 22.6g 7-AVCA, 43g cefdinir side chain active ester and 150 ml tetrahydrofuran. Control temperature 20 °C-23 °C. Add dropwise 12g triethylamine. Stir the reaction for 5h. HPLC measured end point of the reaction. After the reaction is complete, add 200 ml dichloromethane, anisole 30 ml. Cool to -25 °C- -20 °C. Place the dry hydrogen chloride gas. After about 1.5h, HPLC measured end point of the reaction. After the reaction, through N₂In the system away excess hydrogen chloride gas, the temperature of not more than 0 °C, dropwise 5percent of K₂CO₃, Control pH value is 5.5 - 6.0, layered, in the aqueous phase by adding 80mLCH₂Cl₂Extraction, layered, in the aqueous phase by adding 2g activated carbon to decolorize 1h, filtering, adding water 400 ml, for 2 mol/L hydrochloric acid to adjust the pH value to 2.2 - 2.4, temperature control 25 °C -28 °C, nourishing crystal 2h after filtering, washing, alcohol washing, drying, to obtain cefdinir 35g, yield 88.6percent, purity of 99.2percent.

Reference： [1] Patent: CN106279207, 2017, A, . Location in patent: Paragraph 0033; 0034; 0035
[2] Patent: WO2005/121154, 2005, A1, . Location in patent: Page/Page column 10
[3] Patent: WO2006/117794, 2006, A1, . Location in patent: Page/Page column 4-5

2
[ 79349-82-9 ]
[ 143183-03-3 ]
[ 91832-40-5 ]

Yield	Reaction Conditions	Operation in experiment
85.8%	Stage #1: With triethylamine In N,N-dimethyl acetamide at 15 - 20℃; for 4 h; Stage #2: With hydrogenchloride; methoxybenzene In dichloromethane; N,N-dimethyl acetamide at -15 - -10℃; for 2 h;	In a dry reaction flask, add 30g 7-AVCA, 85g cefdinir side chain active ester and 100 ml dimethylacetamide. Control temperature at 15 °C -20 °C. Add dropwise 30g triethylamine. Stir the reaction for 4h. The reaction completely becomes clear. After the reaction is complete, add 250 ml dichloromethane. Lower the temperature to -15 °C - -10 °C. Add 50 ml anisole. Place dry hydrogen chloride gas. After about 2h, HPLC measured end point of the reaction, the reaction after the end of the, through N₂Away excess hydrogen chloride gas in the system. Then add 100 ml H₂O, dropping 10percent of Na₂CO₃Solution, adjusting the pH value of 5.5 - 6.0, the temperature does not exceed 5 °C, layered. The aqueous phase is then added to 100 ml CH₂Cl₂Extraction, layered, add aqueous 3g decolorized with active carbon, the decolorization 1h after filtering, adding 500 ml water, for 2 mol/L hydrochloric acid to adjust the pH value to 2.2 - 2.4, temperature control 20 °C -25 °C, nourishing crystal 2h after filtering, washing, alcohol washing, drying, to obtain cefdinir 45g, yield 85.8percent, the purity is ≥ 99percent.

Reference： [1] Patent: CN106279207, 2017, A, . Location in patent: Paragraph 0030; 0031; 0032

3
[ 79349-82-9 ]
[ 91832-40-5 ]

Reference： [1] Patent: US6350869, 2002, B1, . Location in patent: Page column 3

[ 79349-82-9 ] Synthesis Path-Downstream 1~3

1
2-(Z)-(2-aminothiazol-4-yl)-2-hydroxyiminoacetic acid chloride/hydrochloride [ No CAS ]
[ 79349-82-9 ]
[ 91832-40-5 ]

Reference： [1]Patent: US6350869,2002,B1 .Location in patent: Page column 3

2
[ 104797-47-9 ]
[ 79349-82-9 ]
[ 91832-40-5 ]

Yield	Reaction Conditions	Operation in experiment
88.6%		In a dry reaction flask, add 22.6g 7-AVCA, 43g cefdinir side chain active ester and 150 ml tetrahydrofuran. Control temperature 20 C-23 C. Add dropwise 12g triethylamine. Stir the reaction for 5h. HPLC measured end point of the reaction. After the reaction is complete, add 200 ml dichloromethane, anisole 30 ml. Cool to -25 C- -20 C. Place the dry hydrogen chloride gas. After about 1.5h, HPLC measured end point of the reaction. After the reaction, through N2In the system away excess hydrogen chloride gas, the temperature of not more than 0 C, dropwise 5% of K2CO3, Control pH value is 5.5 - 6.0, layered, in the aqueous phase by adding 80mLCH2Cl2Extraction, layered, in the aqueous phase by adding 2g activated carbon to decolorize 1h, filtering, adding water 400 ml, for 2 mol/L hydrochloric acid to adjust the pH value to 2.2 - 2.4, temperature control 25 C -28 C, nourishing crystal 2h after filtering, washing, alcohol washing, drying, to obtain cefdinir 35g, yield 88.6%, purity of 99.2%.
		10.0 grams (44.2 mmol) of 7-amino-3-vinyl-3-cephem-4-carboxylic acid and 18.0 grams ( 44.7mmol) of (Z) - (2-amionthiazol-4-yl) -2-acetoxyiminoacetic acid 2- benzothiazolyl thioester were suspended in 100ml tetrahydrofuran and 40 ml DM water at room temperature and 4.7 grams (46.5mmol) of triethylamine was added. Then, the reaction mixture was stirred for 4-6 hrs at ambient temperature and 70 ml dichloromethane was added to reaction mixture and stirred for 10-30 minutes. Layers were separated and the aqueous layer treated with carbon, filtered, adjusted to pH 8.0- 8.2 with potassium carbonate solution, and the mixture stirred for 30-45 minutes at room temperature. The pH of the solution adjusted to 2-2.5 with sulfuric acid. The product obtained was filtered off, washed with water and dried to obtain 7-(Z)-[2-(2- amino-thiazol-4-yl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylic acid in a purity of 95%.
		Example 1; Step-I:T-Amino-S-vinyl-S-cephem^-carboxylic acid (40 gm) and 2-mercapto-1 ,3- benzothiazolyl-(Z)-2-(2-aminothiazol-4-yl)-2-(acetyloxyimino)-acetate (80 gm) are added to tetrahydrofuran (400 ml), stirred for 10 minutes, water (200 ml) is added at 250C and then the contents are cooled to 15 - 200C. Triethylamine (20 gm) is added and stirred for 3 - 4 hours at 15 - 200C. To the reaction mass methylenedichloride (400 ml) is added at 15 - 200C, stirred for 15 minutes and separated the organic layer. Aqueous layer is treated with activated carbon (4 gm) for 30 minutes while degassing. Filtered over hyflo bed and adjusted the pH of the aqueous layer to 8.1 - 8.5 with K2CO3 solution. Ammonium chloride (26.5 gm) is added and stirred at 20 - 250C for 30 minutes while maintaining the pH at 8.0 - 8.2. The temperature is raised to 35 - 400C, pH is adjusted to 2.4 - 2.5 with 50% sulfuric acid and stirred for 2 hours at the same temperature. Filtered EPO <DP n="7"/>the solid, washed with water (400 ml) and dried under vacuum at 40 - 45 C to give 60 gm of crude cefdinir (HPLC purity: 98.1%).

Reference： [1]Patent: CN106279207,2017,A .Location in patent: Paragraph 0033; 0034; 0035
[2]Patent: WO2005/121154,2005,A1 .Location in patent: Page/Page column 10
[3]Patent: WO2006/117794,2006,A1 .Location in patent: Page/Page column 4-5

3
[ 79349-82-9 ]
[ 143183-03-3 ]
[ 91832-40-5 ]

Yield	Reaction Conditions	Operation in experiment
85.8%		In a dry reaction flask, add 30g 7-AVCA, 85g cefdinir side chain active ester and 100 ml dimethylacetamide. Control temperature at 15 C -20 C. Add dropwise 30g triethylamine. Stir the reaction for 4h. The reaction completely becomes clear. After the reaction is complete, add 250 ml dichloromethane. Lower the temperature to -15 C - -10 C. Add 50 ml anisole. Place dry hydrogen chloride gas. After about 2h, HPLC measured end point of the reaction, the reaction after the end of the, through N2Away excess hydrogen chloride gas in the system. Then add 100 ml H2O, dropping 10% of Na2CO3Solution, adjusting the pH value of 5.5 - 6.0, the temperature does not exceed 5 C, layered. The aqueous phase is then added to 100 ml CH2Cl2Extraction, layered, add aqueous 3g decolorized with active carbon, the decolorization 1h after filtering, adding 500 ml water, for 2 mol/L hydrochloric acid to adjust the pH value to 2.2 - 2.4, temperature control 20 C -25 C, nourishing crystal 2h after filtering, washing, alcohol washing, drying, to obtain cefdinir 45g, yield 85.8%, the purity is ? 99%.

Reference： [1]Patent: CN106279207,2017,A .Location in patent: Paragraph 0030; 0031; 0032

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Technical Information

? Acyl Group Substitution ? Arndt-Eistert Homologation ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bucherer-Bergs Reaction ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Fischer Indole Synthesis ? Grignard Reaction ? Halogenation ? Heat of Combustion ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hunsdiecker-Borodin Reaction ? Hydride Reductions ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? Mannich Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Preparation of Carboxylic Acids ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions of Carboxylic Acids ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Specialized Acylation Reagents-Vilsmeier Reagent ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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[ 79349-82-9 ]

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H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 79349-82-9 ] {[proInfo.proName]}

Quality Control of [ 79349-82-9 ]

Related Doc. of [ 79349-82-9 ]

Product Details of [ 79349-82-9 ]

Calculated chemistry of [ 79349-82-9 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 79349-82-9 ]

Application In Synthesis of [ 79349-82-9 ]

[ 79349-82-9 ] Synthesis Path-Upstream 1~3

[ 79349-82-9 ] Synthesis Path-Downstream 1~3

Technical Information

Related Functional Groups of [ 79349-82-9 ]

Amides

Amines

Carboxylic Acids

Related Parent Nucleus of [ 79349-82-9 ]

Other Aliphatic Heterocycles

Precautionary Statements-General

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Physical hazards

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Inquiry

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[ 79349-82-9 ]

Related Parent Nucleus of
[ 79349-82-9 ]