[ CAS No. 141699-55-0 ] {[proInfo.proName]}

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2D 3D

Structure of 141699-55-0 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 141699-55-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 141699-55-0 ]

SDS Specification

Alternatived Products of [ 141699-55-0 ]

Product Details of [ 141699-55-0 ]

CAS No. :	141699-55-0	MDL No. :	MFCD04115305
Formula :	C₈H₁₅NO₃	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	XRRXRQJQQKMFBC-UHFFFAOYSA-N
M.W :	173.21	Pubchem ID :	2756801
Synonyms :		Chemical Name :	tert-Butyl 3-hydroxyazetidine-1-carboxylate

Calculated chemistry of [ 141699-55-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.88
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	48.14
TPSA :	49.77 ?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) :	-7.16 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.09
Log Po/w (XLOGP3) :	0.27
Log Po/w (WLOGP) :	0.22
Log Po/w (MLOGP) :	0.24
Log Po/w (SILICOS-IT) :	-0.01
Consensus Log Po/w :	0.56

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.89
Solubility :	22.5 mg/ml ; 0.13 mol/l
Class :	Very soluble
Log S (Ali) :	-0.88
Solubility :	23.0 mg/ml ; 0.133 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.14
Solubility :	127.0 mg/ml ; 0.731 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.08

Safety of [ 141699-55-0 ]

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

Application In Synthesis of [ 141699-55-0 ]

* 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 [ 141699-55-0 ]
Downstream synthetic route of [ 141699-55-0 ]

[ 141699-55-0 ] Synthesis Path-Upstream 1~1

1
[ 141699-55-0 ]
[ 1104083-23-9 ]

Reference： [1] Patent: US2015/5280, 2015, A1,
[2] Patent: US2015/368238, 2015, A1,

[ 141699-55-0 ] Synthesis Path-Downstream 1~10

1
[ 454-16-0 ]
[ 141699-55-0 ]
[ 960401-34-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium tert-butylate; In tetrahydrofuran; at 0℃; for 0.5h;	Dissolve l-fluoro-2-methoxy-4-nitro-benzene (118 g, 689 mmol) and 3-hydroxy- azetidine-1-carboxylic acid tert-bupsilonXyl ester (125 g, 724 mmol) in THF (800 mL) and cool to 0 0C under nitrogen. To the above solution, add dropwise a 1 M THF solution of tert- BuOK (1 L). After the addition is complete, stir the dark brown solution for 30 min at 0 0C and then dilute with water (1 L) over a 10 min period. Stir the mixture for 5 min, then extract with tert-bvAyl methyl ether (2x ). Combine the organic solutions and wash with brine (2 x 700 mL), then dry and concentrate. Dry the solid in vacuo at 45 0C for 20 h to obtain 216 g (95percent) of the title compound as a yellow solid. 1H NMR (300 MHz, CDCl3) 6.47 (d, IH, J= 8.5), 6.30 (d, IH, J= 2.6), 6.17 (dd, IH, J= 2.4, 8.5), 4.76 (m, IH), 4.18 (m, 2H), 4.04 (m, 2H), 3.80 (s, 3H), 1.42 (s, 9H).
95%	With potassium tert-butylate; In tetrahydrofuran; at 0℃; for 0.5h;	Preparation 60; 3-(2-Methoxy-4-nitro-phenoxy)-azetidine-l-carboxylic acid tert-butyl ester; Dissolve l-fluoro-2-methoxy-4-nitro-benzene (118 g, 689 mmol) and 3 -hydroxy - azetidine-1-carboxylic acid tert-butyl ester (125 g, 724 mmol) in THF (800 mL) and cool to 0 0C. To the above solution under a nitrogen atmosphere, add dropwise a IM solution of tBuOK (I L, solution in THF). After addition is complete, stir the dark brown solution for 30 min at 0 0C, then dilute with water (1 L) over a 10 min period. Stir the mixture for5 min, then extract with MTBE twice. Combine the organic solutions and wash with brine (2 x 700 mL), then dry and concentrate. Dry the solid in vacuo at 45 0C for 20 h to <n="56"/>obtain 216 g (95percent) of the title compounds as a yellow solid. 1H NMR (300 MHz, CDCl3) .pound. 1.42 (s, 9H), 3.80 (s, 3H), 4.04 (m, 2H), 4.18 (m, 2H), 4.76 (m, IH), 6.17 (dd, IH, J = 2.4, 8.5), 6.30 (d, IH, J= 2.6), 6.47 (d, IH, J= 8.5).

Reference： [1]Patent: WO2008/76562,2008,A1 .Location in patent: Page/Page column 25
[2]Patent: WO2007/146758,2007,A2 .Location in patent: Page/Page column 54-55

2
[ 16427-44-4 ]
[ 141699-55-0 ]
N-tert-Butoxycarbonyl-3-(2-methoxyethoxy)azetidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide;	Reference example 4 N-tert-Butoxycarbonyl-3-(2-methoxyethoxy)azetidine To a suspension of 0.25 g of 60% sodium hydride in 5 ml of dried N,N-dimethylformamide, a solution of 1.00 g of N-tert-butoxycarbonyl-3-azetidinol in 3 ml of dried N,N-dimethylformamide was added under stirring at room temperature. The mixture was stirred at room temperature for 30 minutes, then added dropwise with a solution of 0.98 g of <strong>[16427-44-4]2-methoxyethyl methanesulfonate</strong> in 2 ml of dried N,N-dimethylformamide, and stirred at the same temperature for 4 hours. The reaction solution was poured into ice water, and extracted with ethyl acetate. The extract was washed successively with water and saturated brine, and dried over sodium sulfate, and then the solvent was evaporated under reduced pressure. Theresidue was purified by column chromatography (silica gel, ethyl acetate: n-heptane = 1: 3) to obtain 0.67 g of a colorless liquid. NMR spectrum (DMSO-d6) delta ppm: 1.37(9H,s),3.25(3H,s),3.41-3.45(2H,m),3.46-3.49(2H,m),3.64(2H,dd,J=9,4Hz),3.98(2H,d d,J=9,6.5Hz),4.21-4.26(1H,m) IR spectrum nu (liq.) cm-1: 1706

Reference： [1]Patent: EP1130016,2001,A1

3
[ 141699-55-0 ]
[ 103291-07-2 ]
[ 1035219-86-3 ]

Yield	Reaction Conditions	Operation in experiment
46%		Add sodium hydride (2.77 g, 60% w/w, 69.2 mmol) to a solution of 3-hydroxy- azetidine-1-carboxylic acid tert-butyl ester (10.9 g, 62.9 mmol) in dimethyl sulfoxide (100 mL). Stir the mixture for 30 min and then add 3-bromo-6-fluoroanisole (15.5 g, 75.5 mmol). Heat the mixture to 65 0C overnight. Cool the mixture to room temperature and then dilute the solution with saturated ammonium chloride and brine and extract with ethyl acetate. Wash the organics five times with brine, then dry over sodium sulfate and filter. Concentrate and purify via silica gel chromatography using a 0-45% gradient of ethyl acetate/hexane to give 10.4 g (46%) of the title compound as a clear oil.

Reference： [1]Patent: WO2008/76562,2008,A1 .Location in patent: Page/Page column 50

4
[ 392-71-2 ]
[ 141699-55-0 ]
[ 1266334-31-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 479 - 483

5
[ 141699-55-0 ]
[ 877399-35-4 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 6342 - 6363
[2]Journal of Medicinal Chemistry,2011,vol. 54,p. 6342 - 6363
[3]Patent: WO2020/215094,2020,A1

6
[ 612501-52-7 ]
[ 141699-55-0 ]
[ 1441146-93-5 ]

Reference： [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 742 - 746

7
[ 141699-55-0 ]
[ 889952-83-4 ]

Reference： [1]Patent: WO2013/149121,2013,A1
[2]Patent: WO2017/27684,2017,A1

8
[ 313340-08-8 ]
[ 141699-55-0 ]
tert-butyl 3-[(5-carbamoyl-6-chloro-3-ethylpyrazin-2-yl)oxy]azetidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
318 mg		Preparation Example 352 To a mixture of tert-butyl 3-hydroxyazetidine-1-carboxylate (420 mg) and N,N-dimethylformamide (12.5 mL) was added potassium tert-butoxide (260 mg) under ice-cooling, followed by stirring for 1 hour, and then <strong>[313340-08-8]3,5-dichloro-6-ethylpyrazine-2-carboxamide</strong> (500 mg) was added thereto, followed by stirring for 1 hour. The reaction mixture was poured into ice water, followed by extraction with ethyl acetate. The organic phase was washed with saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate), and then washed with a mixed solvent of hexane:diisopropyl ether to obtain tert-butyl 3-[(5-carbamoyl-6-chloro-3-ethylpyrazin-2-yl)oxy]azetidine-1-carboxylate (318 mg) as a white solid.

Reference： [1]Patent: US2014/323463,2014,A1 .Location in patent: Paragraph 0394

9
[ 141699-55-0 ]
[ 1064194-10-0 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 6160 - 6163

10
[ 261952-16-3 ]
[ 141699-55-0 ]
3-[[2-methyl-3-(trifluoromethyl)phenyl]methoxy]azetidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid; In dichloromethane; at 20℃; for 3h;Inert atmosphere;	General procedure: To a solution of tert-butyl 3 -((2 -fluoro-4-(trifluoromethoxy)benzyl)oxy)azetidine- 1 -carboxylate(415 mg, 1.14 mmol) in DCM (5 mL) was added TFA (1.3 g, 875 tL, 11.4 mmol) and thereaction mixture was stirred at RT for 3 h. Volatiles were removed in vacuo to yield 455 mg oflight yellow oil that was used in the next step without further purification. MS (ESI): mlz =266.1 [M+H].

Reference： [1]Patent: WO2020/35425,2020,A1 .Location in patent: Page/Page column 64; 171; 179

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Technical Information

? Acyl Group Substitution ? Appel Reaction ? Bouveault-Blanc Reduction ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Catalytic Hydrogenation ? Chan-Lam Coupling Reaction ? Chugaev Reaction ? Complex Metal Hydride Reductions ? Corey-Kim Oxidation ? Dess-Martin Oxidation ? Ester Cleavage ? Hydride Reductions ? Jones Oxidation ? Lawesson's Reagent ? Martin's Sulfurane Dehydrating Reagent ? Mitsunobu Reaction ? Moffatt Oxidation ? Oxidation of Alcohols by DMSO ? Preparation of Alcohols ? Preparation of Amines ? Reactions of Alcohols ? Reactions of Amines ? Reactions with Organometallic Reagents ? Ritter Reaction ? Sharpless Olefin Synthesis ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Swern Oxidation

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[ 141699-55-0 ]

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[ 941685-26-3 ]

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Ghs Precautionary Statements

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Code	Phrase
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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
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H260	In contact with water releases flammable gases which may ignite spontaneously
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H316	Causes mild skin irritation
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H320	Causes eye irritation
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H333	May be harmful if inhaled
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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. 141699-55-0 ] {[proInfo.proName]}

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[ 141699-55-0 ] Synthesis Path-Upstream 1~1

[ 141699-55-0 ] Synthesis Path-Downstream 1~10

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Baricitinib Related Intermediates

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Alcohols

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Aliphatic Heterocycles

Azetidines

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[ 141699-55-0 ]

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[ 141699-55-0 ]