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【结 构 式】

【分子编号】45019

【品名】tert-butyl (3R,6S,7aS)-5-oxo-3-phenyltetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-6-ylcarbamate

【CA登记号】

【 分 子 式 】C17H22N2O4

【 分 子 量 】318.37276

【元素组成】C 64.13% H 6.97% N 8.8% O 20.1%

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:(XIV)

In a related procedure, the protected pyrrolidinone (II) was treated with 2,4,6-triisopropylbenzenesulfonyl azide and LDA to produce a 1:3.2 mixture of isomeric azides (XI) and (XII). After isolation of the major cis-isomer (XII), its catalytic hydrogenation over Pd/C yielded amine (XIII), which was subsequently protected as the N-Boc derivative (XIV). Reductive cleavage of the benzylidene group of (XIV) using Li in liquid ammonia provided the (hydroxymethyl)pyrrolidinone (XV). Reduction of the hydroxymethyl group to the methyl derivative (X) was effected via iodide (XVI) in a similar sequence as above.

1 Nakanishi, T.; Otsuka, T.; Hashimoto, S.; Okamoto, M.; Muramatsu, Y.; Hino, M.; Hatanaka, H.; WF14865A and B, new cathepsins B and L inhibitors produed by Aphanoascus fulvescens. I. Taxomy, production, purification and biological properties. J Antibiot 2000, 53, 5, 449.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(II) 38561 (3R,7aS)-3-phenyltetrahydro-5H-pyrrolo[1,2-c][1,3]oxazol-5-one 103201-79-2 C12H13NO2 详情 详情
(X) 45015 tert-butyl (3S,5R)-5-methyl-2-oxopyrrolidinylcarbamate C10H18N2O3 详情 详情
(XI) 45016 (3R,6R,7aS)-6-azido-3-phenyltetrahydro-5H-pyrrolo[1,2-c][1,3]oxazol-5-one C12H12N4O2 详情 详情
(XII) 45017 (3R,6S,7aS)-6-azido-3-phenyltetrahydro-5H-pyrrolo[1,2-c][1,3]oxazol-5-one C12H12N4O2 详情 详情
(XIII) 45018 (3R,6S,7aS)-6-amino-3-phenyltetrahydro-5H-pyrrolo[1,2-c][1,3]oxazol-5-one C12H14N2O2 详情 详情
(XIV) 45019 tert-butyl (3R,6S,7aS)-5-oxo-3-phenyltetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-6-ylcarbamate C17H22N2O4 详情 详情
(XV) 45020 tert-butyl (3S,5S)-5-(hydroxymethyl)-2-oxopyrrolidinylcarbamate C10H18N2O4 详情 详情
(XVI) 45021 tert-butyl (3S,5S)-5-(iodomethyl)-2-oxopyrrolidinylcarbamate C10H17IN2O3 详情 详情
Extended Information