(1S,3aR,6aS)-2-[(2S)-2-[[(2S)-2-Amino-2-cyclohexylacetyl]amino]-3,3-dimethyl-1-oxobutyl]octahydrocyclopenta[c]pyrrole-1-carboxylic acid tert-butyl ester -Drug Synthesis Database

【结构式】

【分子编号】65433

【品名】(1S,3aR,6aS)-2-[(2S)-2-[[(2S)-2-Amino-2-cyclohexylacetyl]amino]-3,3-dimethyl-1-oxobutyl]octahydrocyclopenta[c]pyrrole-1-carboxylic acid tert-butyl ester

【CA登记号】926276-18-8

【分子式】C₂₆H₄₅N₃O₄

【分子量】463.66112

【元素组成】C 67.35% H 9.78% N 9.06% O 13.8%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(XIX)

An alternative route to the precursor N-acyl tripeptide (VIII) consists of coupling of N-Cbz-L-tert-leucine (XIII) with the bicyclic amino ester (XIV) to afford the protected dipeptide (XV), from which the N-Cbz group is removed by catalytic hydrogenolysis over Pearlman’s catalyst, yielding (XVI). The dipeptide ester (XVI) is then coupled with N-Cbz-L-cyclohexylglycine (XVII) to give (XVIII), which is further deprotected by catalytic hydrogenolysis to afford the tripeptide ester (XIX). After acylation of (XIX) with pyrazinecarboxylic acid (III) employing CDI, the resulting N-acyl tripeptide tert-butyl ester (XX) is treated with HCl in formic acid to provide the target intermediate (VIII) (3). Scheme 2.

参考文献中间体

合成目标

【3】 Tanoury, G.J., Chen, M., Cochran, J.E. (Vertex Pharmaceuticals, Inc.). Processes and intermediates. WO 2007022459.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(III)	37256	2-pyrazinecarboxylic acid; Pyrazinoic acid	98-97-5	C₅H₄N₂O₂	详情	详情
(VIII)	65423	(1S,3aR,6aS)-(2S)-2-Cyclohexyl-N-(pyrazinylcarbonyl)glycyl-3-methyl-L-valyloctahydrocyclopenta[c]pyrrole-1-carboxylic acid	402958-98-9	C₂₇H₃₉N₅O₅	详情	详情
(XIII)	65427	Cbz-L-tert-Leucine; (S)-N-Cbz-2-amino-3,3-dimethyl-butyric acid	62965-10-0	C₁₄H₁₉NO₄	详情	详情
(XIV)	65428	(1S,3aR,6aS)-Octahydrocyclopenta[c]pyrrole-1-carboxylic acid tert-butyl ester	714194-68-0	C₁₂H₂₁NO₂	详情	详情
(XV)	65429	(1S,3aR,6aS)-2-[(2S)-3,3-Dimethyl-1-oxo-2-[[(phenylmethoxy)carbonyl]amino]butyl]octahydrocyclopenta[c]pyrrole-1-carboxylic acid tert-butyl ester	926276-15-5	C₂₆H₃₈N₂O₅	详情	详情
(XVI)	65430	(1S,3aR,6aS)-2-[(2S)-2-Amino-3,3-dimethyl-1-oxobutyl]octahydrocyclopenta[c]pyrrole-1-carboxylic acid tert-butyl ester	926276-16-6	C₁₈H₃₂N₂O₃	详情	详情
(XVII)	65431	Cbz-Cyclohexyl-L-glycine; (S)-Cbz-Cyclohexylglycine; (S)-N-Cbz-Aminocyclohexylacetic acid	69901-75-3	C₁₆H₂₁NO₄	详情	详情
(XVIII)	65432	(1S,3aR,6aS)-2-[(2S)-2-[[(2S)-2-Cyclohexyl-2-[[(phenylmethoxy)carbonyl]amino]acetyl]amino]-3,3-dimethyl-1-oxobutyl]octahydrocyclopenta[c]pyrrole-1-carboxylic acid tert-butyl ester	926276-17-7	C₃₄H₅₁N₃O₆	详情	详情
(XIX)	65433	(1S,3aR,6aS)-2-[(2S)-2-[[(2S)-2-Amino-2-cyclohexylacetyl]amino]-3,3-dimethyl-1-oxobutyl]octahydrocyclopenta[c]pyrrole-1-carboxylic acid tert-butyl ester	926276-18-8	C₂₆H₄₅N₃O₄	详情	详情
(XX)	65434	(1S,3aR,6aS)-2-[(2S)-2-[[(2S)-2-Cyclohexyl-2-[(2-pyrazinylcarbonyl)amino]acetyl]amino]-3,3-dimethyl-1-oxobutyl]octahydrocyclopenta[c]pyrrole-1-carboxylic acid tert-butyl ester	926276-19-9	C₃₁H₄₇N₅O₅	详情	详情

Extended Information