• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】35563

【品名】N(1)-[(1R)-4-azido-1-[(1R,2S,6R,8R)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]butyl]-N(1)-phenethyl-1,1-cyclopentanedicarboxamide

【CA登记号】

【 分 子 式 】C29H42BN5O4

【 分 子 量 】535.49478

【元素组成】C 65.05% H 7.91% B 2.02% N 13.08% O 11.95%

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:(XV)

Carbethoxylation of cyclopentanecarboxylic acid (VIII) with ethyl chloroformate and LDA afforded monoethyl cyclopentane-1,1-dicarboxylate (IX), which was coupled with phenethylamine (X) in the presence of TBTU, yielding amide (XI). Subsequent saponification of the ethyl ester group of (XI) gave carboxylic acid (XII), which was activated as the mixed anhydride (XIII) with isobutyl chloroformate and triethylamine. Coupling of this anhydride with aminoboronate (VII) produced the bisamide (XIV). After displacement of the bromine of (XIV) with NaN3, the resulting azide (XV) was reduced to amine (XVI) by hydrogenation over Pd/C. The required guanidine (XVII) was then obtained by condensation of (XVI) with cyanamide in refluxing EtOH. Finally, cleavage of the boronate ester by exchange with phenylboronic acid in the presence of benzenesulfonic acid furnished the title compound.

1 Verbeuren, T.; Rupin, A.; De Nanteuil, G.; Gloanec, P.; New dicarbonyl cycloalkyl based thrombin inhibitors with improved activity and selectivity compared to (D)-Phe-Pro-boroArg derivatives . 218th ACS Natl Meet (Aug 22 1999, New Orleans) 1999, Abst MEDI 201.
2 Gloanec, P.; Portevin, B.; Lila, C.; Rupin, A.; de Nanteuil, G.; Simonet, S.; Verbeuren, T. (ADIR et Cie.); Cpds. derived from boronic acid. EP 0792883; FR 2745288; US 5814622 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VI) 35561 (1R)-4-bromo-1-[(1R,2S,6R,8R)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]-1-butanamine; (1R)-4-bromo-1-[(1R,2S,6R,8R)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]butylamine C14H25BBrNO2 详情 详情
(VIII) 20734 cyclopentanecarboxylic acid 3400-45-1 C6H10O2 详情 详情
(IX) 32539 1-(ethoxycarbonyl)cyclopentanecarboxylic acid C9H14O4 详情 详情
(X) 18333 Phenethylamine; 2-Phenyl-1-ethanamine 64-04-0 C8H11N 详情 详情
(XI) 32540 ethyl 1-[(phenethylamino)carbonyl]cyclopentanecarboxylate C17H23NO3 详情 详情
(XII) 32541 1-[(phenethylamino)carbonyl]cyclopentanecarboxylic acid C15H19NO3 详情 详情
(XIII) 32542 1-[N-(2-Phenylethyl)carbamoyl]cyclopentylcarbonyl isobutoxycarbonyl anhydride C20H27NO5 详情 详情
(XIV) 35562 N(1)-[(1R)-4-bromo-1-[(1R,2S,6R,8R)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]butyl]-N(1)-phenethyl-1,1-cyclopentanedicarboxamide C29H42BBrN2O4 详情 详情
(XV) 35563 N(1)-[(1R)-4-azido-1-[(1R,2S,6R,8R)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]butyl]-N(1)-phenethyl-1,1-cyclopentanedicarboxamide C29H42BN5O4 详情 详情
(XVI) 35564 N(1)-[(1R)-4-amino-1-[(1R,2S,6R,8R)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]butyl]-N(1)-phenethyl-1,1-cyclopentanedicarboxamide C29H44BN3O4 详情 详情
(XVII) 35565 N(1)-[(1R)-4-[[amino(imino)methyl]amino]-1-[(1R,2S,6R,8R)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]butyl]-N(1)-phenethyl-1,1-cyclopentanedicarboxamide C30H46BN5O4 详情 详情
Extended Information