(3R,6S,7aS)-6-azido-3-phenyltetrahydro-5H-pyrrolo[1,2-c][1,3]oxazol-5-one -Drug Synthesis Database

【结构式】

【分子编号】45017

【品名】(3R,6S,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%

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：(XII)

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.

参考文献中间体

合成目标

【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