Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | ||||||
{[ item.p_purity ]} | {[ item.pr_size ]} | Inquiry |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price) ]} |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]} | {[ item.pr_usastock ]} | in stock Inquiry - | {[ item.pr_chinastock ]} | {[ item.pr_remark ]} in stock Inquiry - | Login | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
CAS No. : | 159622-10-3 | MDL No. : | MFCD11042412 |
Formula : | C11H17NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RFAQWADNTLIWMG-RDDDGLTNSA-N |
M.W : | 227.26 | Pubchem ID : | 10376443 |
Synonyms : |
|
Chemical Name : | (1R,2S)-1-((tert-Butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylic acid |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With 10 wt% Pd(OH)2 on carbon; hydrogen; In tert-butyl methyl ether; under 760.051 Torr; for 3h; | 2 was prepared by a modification of the procedure published in the literature (J. Org. Chem., 2005, 70, 5869). 1 (1.004 g, 4.40 mmol) was dissolved in TI3ME (25 ml) and hydrogenated (1 atm hydrogen gas) over 20percent Pd(OH)2/C (150 mgs)for 3 hours. The suspension was then filtered on celite and thecrude concentrated under reduced pressure. The crude is crystallized from water-ethanol. The crude is taken in 100 ml water and heated to 70° C. and ethanol is added drop wise until the solution becomes cleat The solution is lefi overnight to cool and the solids are filtered to get the pure product 2 (494 mgs, 2.155 mmol, 49percent yield). The pure product is dried under vacuum. |
42% | With hydrogen;palladium hydroxide on carbon; In tert-butyl methyl ether; at 20℃; under 760.051 Torr; for 5h;Product distribution / selectivity; | Compound 23; (1R,2R )-1-(tert-butoxycarbonylamino)-2-ethy]cyclopropanecarboxylic acid; (1R,2S)-1-(tert-butoxycarbonyl)-2-vinylcyclopropanecarboxyhc acid (10 0 g, 44 0 mmol, prepared as described in WO2005037214) was dissolved m MTBE (250 mL) and hydrogenated (1 atm H2) over Pd(OH)2/C (1 24 g, 8.80 mmol) for 5 h at rt The reaction was then stopped, filtered and concentrated down to 30 mL, followed by addition of 300 mL hexanes while stirring vigorously After 60 mm, the fine white precipitate was filtered, yielding the titled compound as a fine off-white powder (4 2 g, 42 percent yield) 1H-NMR (400 MHz, d6-DMSO) delta 12 2 (s, 1 H), 7 41 (s, 1 H), 1.29 - 1 54 (m, 3 H), 1 36 (s, 9 H), 1 18 - 1 21 (m, 1 H), 0 96 - 0 98 (m, 1 H), 0 90 (t, 3 H); (1R,2R)-1-(tert-butoxycarbonylamino)-2-ethylcyclopropanecarboxylic acid; (li,25)-1-(tert-butoxycarbonyl)-2-vinyIcyclopropanecarboxylic acid (10.0 g, 44.0 mmol, prepared as described in WO2005037214) was dissolved in MTBE (250 mL) and hydrogenated (1 atm H2) over Pd(OH)2/C (1.24 g, 8.80 mmol) for 5 h at rt. The reaction was then stopped, filtered and concentrated down to 30 mL, followed by addition of 300 mL hexanes while stirring vigorously. After 60 min, the fine white precipitate was filtered, yielding the titled compound as a fine off-white powder (4.2 g, 42 percent yield). 1H-NMR (400 MHz, d6-DMSO) delta 12.2 (s, 1 H), 7.41 (s, 1 H), 1.29 - 1.54 (m, 3 H), 1.36 (s, 9 H), 1.18 - 1.21 (m, 1 H), 0.96 - 0.98 (m, 1 H), 0.90 (t, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | The vinylcyclopropyl ester 1c (9.23 g, 38.3 mmol) was dissolved in THF (127 mL) and MeOH (127 mL). Aqueous lithium hydroxide solution (1.5 N, 127 mL, 202 mmol) was added at a fast dropwise pace. After 2 h at room temperature, more lithium hydroxide (4.6 g, 202 mmol) was added, and the suspension was stirred at room temperature for an additional 17 h. The suspension was cooled to 0° C. and acidified to pH 5 with 1N HCl, whereupon ethyl acetate (300 mL) was added. It was further acidified to pH 1 and extracted with ethyl acetate (2.x.300 mL). The combined organic layers were washed with brine (200 mL), dried over magnesium sulfate, and concentrated in vacuo to afford 8.91 g of the acid 1d in quantitative yield. | |
98% | With lithium hydroxide monohydrate; water; In tetrahydrofuran; methanol; at 45℃; | Ste 1: (lR,2S)-l-((tert-butoxycarbonyl)amino)-2-vin lcyclopropanecarboxylic A round-bottom flask was charged with (lR,2S)-ethyl l-((tert- butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylate (4 g, 15.67 mmol) and lithium hydroxide monohydrate (2.63 g, 62.7 mmol). Methanol (52.2 ml), THF (52.2 ml) and water (52.2 ml) were added. The mixture was heated (oil bath at 45°C) overnight. The reaction mixture was concentrated to half-its volume in rotavap and the pH of the mixture was adjusted to pH = 2-3 with aq 1M HC1. The mixture was extracted with dichloromethane (3 x 150 mL). The combined organic extracts were washed with brine (50 mL), dried over magnesium sulfate, filtered and concentrated in rotavap to give the title compound (3.5 g, 15.40 mmol, 98 percent yield) as a white powder. No further purification was carried out. |
[ 259217-95-3 ]
(1R,2S)-Ethyl 1-((tert-butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylate
Similarity: 0.94
[ 120728-10-1 ]
1-((tert-Butoxycarbonyl)amino)cyclobutanecarboxylic acid
Similarity: 0.90
[ 35264-09-6 ]
1-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid
Similarity: 0.90
[ 155976-13-9 ]
(S)-2-((tert-Butoxycarbonyl)amino)-2-cyclopropylacetic acid
Similarity: 0.90
[ 609768-49-2 ]
(R)-2-((tert-Butoxycarbonyl)amino)-2-cyclopropylacetic acid
Similarity: 0.90