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【结 构 式】

【分子编号】27164

【品名】benzyl 1-((1S)-1-azido-2-[[(1R)-1-ethyl-2,2-dimethylpropyl]amino]-2-oxoethyl)cyclopentanecarboxylate

【CA登记号】

【 分 子 式 】C22H32N4O3

【 分 子 量 】400.52124

【元素组成】C 65.97% H 8.05% N 13.99% O 11.98%

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:(XXXIII)

The intermediate cyclopentanecarboxylic ester (XII) has been obtained as follows: The reaction of 2-oxaspiro[4.4]nonane-1,3-dione (XXVI) with the chiral auxiliary 4(S)-isopropyloxazolidin-2-one (XXVII) by means of BuLi in THF gives the addition product (XXVIII), which is protected as the benzyl ester (XXIX) with benzylbromide and DBU. The regioselective azidation of (XXIX) with 2,4,6-triisopropylbenzenesulfonyl azide and potassium bis(trimethylsilyl)amide affords the (S)-azide (XXX), which is treated with H2O2 in THF/water to eliminate chiral auxiliary and providing 2(S)-azido-2-[1-(benzyloxycarbonyl)cyclopentyl]acetic acid (XXXI). Condensation of (XXXI) with 1(R)-ethyl-2,2-dimethylpropylamine (XXXII) by means of HBTU in dichloromethane gives the corresponding amide (XXXIII), which is finally reduced at the azido group with SnCl2 in methanol to afford the target intermediate (XII). The intermediate 1(R)-ethyl-2,2-dimethylpropylamine (XXXII) has been obtained as follows: The reaction of 2,2-dimethyl-3-pentanone (XXXIV) with the chiral auxiliary 1(R)-phenylethylamine (XXXV) by means of TiCl4 in benzene gives N-(1(R)-ethyl-2,2-dimethylpropyl)-N-(1(R)-phenylethyl)amine (XXXVI), which is then hydrogenated with H2 over Pd/C in methanol to eliminate the chiral auxiliary and obtain the target amine (XXXII).

1 Gauthier, J.-A.; Moss, N. (Bio-Mega, Inc.; Boehringer Ingelheim GmbH); Herpes ribonucleotide reductase inhibitors. EP 0837845; JP 1999508246; US 5672586; WO 9700855 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XII) 27151 benzyl 1-((1S)-1-amino-2-[[(1R)-1-ethyl-2,2-dimethylpropyl]amino]-2-oxoethyl)cyclopentanecarboxylate C22H34N2O3 详情 详情
(XXVI) 27158 2-oxaspiro[4.4]nonane-1,3-dione C8H10O3 详情 详情
(XXVII) 12867 (4S)-4-Isopropyl-1,3-oxazolidin-2-one; (R)-4-Isopropyl-2-oxazolidinone 17016-83-0 C6H11NO2 详情 详情
(XXVIII) 27159 1-[2-[(4S)-4-isopropyl-2-oxo-1,3-oxazolidin-3-yl]-2-oxoethyl]cyclopentanecarboxylic acid C14H21NO5 详情 详情
(XXIX) 27160 benzyl 1-[2-[(4S)-4-isopropyl-2-oxo-1,3-oxazolidin-3-yl]-2-oxoethyl]cyclopentanecarboxylate C21H27NO5 详情 详情
(XXX) 27161 benzyl 1-[(1S)-1-azido-2-[(4S)-4-isopropyl-2-oxo-1,3-oxazolidin-3-yl]-2-oxoethyl]cyclopentanecarboxylate C21H26N4O5 详情 详情
(XXXI) 27162 (2S)-2-azido-2-[1-[(benzyloxy)carbonyl]cyclopentyl]ethanoic acid C15H17N3O4 详情 详情
(XXXII) 27163 (1R)-1-ethyl-2,2-dimethylpropylamine C7H17N 详情 详情
(XXXIII) 27164 benzyl 1-((1S)-1-azido-2-[[(1R)-1-ethyl-2,2-dimethylpropyl]amino]-2-oxoethyl)cyclopentanecarboxylate C22H32N4O3 详情 详情
(XXXIV) 27165 2,2-dimethyl-3-pentanone 564-04-5 C7H14O 详情 详情
(XXXV) 10039 (1R)-1-Phenylethylamine; (1R)-1-Phenyl-1-ethanamine.; L-alpha-Phenylethylamine 3886-69-9 C8H11N 详情 详情
(XXXVI) 27166 (3R)-2,2-dimethyl-N-[(1R)-1-phenylethyl]-3-pentanamine C15H25N 详情 详情
Extended Information