CIS-3-BOC-AMINOCYCLOBUTANECARBOXYLIC ACID
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CIS-3-BOC-AMINOCYCLOBUTANECARBOXYLIC ACID
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CAS No:
1008773-79-2
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Formula:
C10H17NO4
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Chemical Name:
CIS-3-BOC-AMINOCYCLOBUTANECARBOXYLIC ACID
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Synonyms:
CIS-3-BOC-AMINOCYCLOBUTANECARBOXYLIC ACID;CIS-3-(TERT-BUTOXYCARBONYLAMINO)CYCLOBUTANECARBOXYLIC ACID;3-Boc-amino-cyclobutanecarboxylic acid;cis-3-(tert-Butoxycarbony...;cis-3-(N-BOC-aMino)cyclobutanecarboxylic acid;(1s,3s)-3-((tert-Butoxycarbonyl)amino)cyclobutanecarboxylic acid;cis-3-[[(1,1-Dimethylethoxy)carbonyl]amino]-Cyclobutanecarboxylic acid
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CAS No:
Characteristics
75.6
1
1.17±0.1 g/cm3(Predicted)
368.3±31.0 °C(Predicted)
H2O: Slightly soluble (4.7 g/L) (25 ºC)
Safety Information
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
CIS-3-BOC-AMINOCYCLOBUTANECARBOXYLIC ACID Use and Manufacturing
To a stirring mixture of cis-3-[[(tert-butoxy)carbonyl]amino]cyclobutane-l-carboxylic acid (100 mg, 0.465 mmol) in DMF (4 mL) was added HATU (212 mg, 0.560 mmol), DIEA (0.230 mL, 1.39 mmol) and 5-cyclohexyl-l, 3-thiazol-2 -amine (93.0 mg, 0.510 mmol) at 25 C. The resulting solution was stirred for 1.5 h at 25 C. The resulting mixture was diluted with water (10 mL) and extracted with DCM (3 x 15 mL). The combined organic layer was washed with brine (4 x 30 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting with 1/1 with ethyl acetate/petroleum ether) to afford tert-butyl N-[cis-3-[(5- cyclohexyl-l, 3-thiazol-2-yl)carbamoyl]cyclobutyl]carbamate as a white solid (98.0 mg). LCMS (ES, m/z): 380 [M+H]+[0078] (ls, 3s)-3-(fert-Butoxycarbonylamino)cyclobutanecarboxylic acid (5. 0 g, 23.2 mmol) was dissolved in dichloromethane (77 mL), cooled to 0 C, and treated with Nu, Omicron- dimethylhydroxylamine hydrochloride (2.95 g, 30.2 mmol) and N-methylmorpholine (3.32 mL, 30.2 mmol) The mixture was stirred for 15 minutes, then EDCI (5.79 g, 30.2 mmol) was added and the reaction was stirred for 18 hours at room temperature. The reaction was cooled to 0 C and quenched with 1 N HC1 (10 mL), then diluted with ethyl acetate, washed successively with aqueous saturated sodium bicarbonate, saturated aqueous sodium chloride, dried over MgS04, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 3-40% ethyl acetate in heptane to afford the desired product (4.34 g, 75%).
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CIS-3-BOC-AMINOCYCLOBUTANECARBOXYLIC ACID
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