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【结 构 式】 
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【分子编号】45016 【品名】(3R,6R,7aS)-6-azido-3-phenyltetrahydro-5H-pyrrolo[1,2-c][1,3]oxazol-5-one 【CA登记号】 |
【 分 子 式 】C12H12N4O2 【 分 子 量 】244.25304 【元素组成】C 59.01% H 4.95% N 22.94% O 13.1% |
合成路线1
该中间体在本合成路线中的序号：(XI)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 |