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【结 构 式】

【分子编号】26849

【品名】tert-butyl (3S)-7,7-dimethyl-2-oxoazepanylcarbamate

【CA登记号】

【 分 子 式 】C13H24N2O3

【 分 子 量 】256.34524

【元素组成】C 60.91% H 9.44% N 10.93% O 18.72%

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:(X)

Removal of phthaloyl protecting group of (VIII) provided amine (IX), which was protected as the tert-butyl carbamate (X) with Boc2O. Alkylation at the lactam nitrogen atom of (X) was then achieved employing LiN(SiMe3)2 and ethyl bromoacetate to afford (XI), which was deprotected under acidic conditions to furnish amine (XII). Alternatively, amine (IX) could be protected using a N-trityl group. Coupling of amine (XII) with 2-(acetylthio)benzenepropanoic acid (XIII) using either BOP or EDC as the condensing reagents produced amide (XIV). Finally, both ethyl ester and acetyl thioester of (XIV) were hydrolyzed with NaOH to yield the title compound.

1 Robl, J.A.; Sulsky, R.; Sieber-McMaster, E.; Ryono DE; Cimarusti MP; Simpkins LM; Karanewsky, D.S.; Chao, S.; Asaad, M.M.; Seymour, A.A.; Fox, M.E.; Smith, P.L.; Trippodo, N.C.; Vasopeptidase inhibitors: Incorporation of geminal and spirocyclic substituted azepinones in mercaptoacyl dipeptides. J Med Chem 1999, 42, 2, 305.
2 Karanewsky, D.S.; Barrish, J.C.; Petrillo, E.W. Jr.; Robl, J.A.; Ryono, D.E. (Bristol-Myers Squibb Co.); Dual action inhibitors. EP 0599444; US 5552397 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VIII) 26847 2-[(3S)-7,7-dimethyl-2-oxoazepanyl]-1H-isoindole-1,3(2H)-dione C16H18N2O3 详情 详情
(IX) 26848 (3S)-3-amino-7,7-dimethyl-2-azepanone C8H16N2O 详情 详情
(X) 26849 tert-butyl (3S)-7,7-dimethyl-2-oxoazepanylcarbamate C13H24N2O3 详情 详情
(XI) 26850 methyl 2-[(6S)-6-[(tert-butoxycarbonyl)amino]-2,2-dimethyl-7-oxoazepanyl]acetate C16H28N2O5 详情 详情
(XII) 26851 methyl 2-[(6S)-6-amino-2,2-dimethyl-7-oxoazepanyl]acetate C11H20N2O3 详情 详情
(XIII) 22493 (2S)-2-(acetylsulfanyl)-3-phenylpropionic acid C11H12O3S 详情 详情
(XIV) 26852 methyl 2-((6S)-6-[[(2S)-2-(acetylsulfanyl)-3-phenylpropanoyl]amino]-2,2-dimethyl-7-oxoazepanyl)acetate C22H30N2O5S 详情 详情
Extended Information