ethyl (2R,4S,5R)-5-[(1R,2S)-1-(acetylamino)-2-methoxy-2-methylpentyl]-4-[(Z)-1-propenyl]-2-pyrrolidinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】55166

【品名】ethyl (2R,4S,5R)-5-[(1R,2S)-1-(acetylamino)-2-methoxy-2-methylpentyl]-4-[(Z)-1-propenyl]-2-pyrrolidinecarboxylate

【CA登记号】

【分子式】C₁₉H₃₄N₂O₄

【分子量】354.49004

【元素组成】C 64.38% H 9.67% N 7.9% O 18.05%

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：(XXIII)

Oxidation of alcohol (XVIII) employing the Dess-Martin periodinane reagent furnished ketone (XIX). Subsequent addition of methylmagnesium bromide to ketone (XIX) gave rise to a mixture of diastereoisomeric carbinols from which alcohol (XX) was isolated as the major isomer. The methyl ether (XXI) was prepared by alkylation of the sodium alkoxide of (XX) with iodomethane in THF. Trifluoroacetic acid-promoted cleavage of the tert-butyl ester and N-Boc protecting groups provided the title compound in the racemic form (+/-)-(XXII). The ethyl ester prepared by esterification of (+/-)-(XXII) with EtOH and SOCl2 was then resolved using chiral HPLC. The desired enantiomer (XXIII) was finally hydrolyzed with LiOH to the title levo carboxylic acid.

参考文献中间体

合成目标

【1】 Inhibitors of neuraminidases. WO 0128996 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XVIII)	55150	di(tert-butyl) (2R,4S,5R)-5-[(1R,2R)-1-(acetylamino)-2-hydroxypentyl]-4-[(Z)-1-propenyl]-1,2-pyrrolidinedicarboxylate	C₂₄H₄₂N₂O₆	详情	详情
(XIX)	55151	di(tert-butyl) (2R,4S,5R)-5-[(1R)-1-(acetylamino)-2-oxopentyl]-4-[(Z)-1-propenyl]-1,2-pyrrolidinedicarboxylate	C₂₄H₄₀N₂O₆	详情	详情
(XX)	55152	di(tert-butyl) (2R,4S,5R)-5-[(1R,2S)-1-(acetylamino)-2-hydroxy-2-methylpentyl]-4-[(Z)-1-propenyl]-1,2-pyrrolidinedicarboxylate	C₂₅H₄₄N₂O₆	详情	详情
(XXI)	55153	di(tert-butyl) (2R,4S,5R)-5-[(1R,2S)-1-(acetylamino)-2-methoxy-2-methylpentyl]-4-[(Z)-1-propenyl]-1,2-pyrrolidinedicarboxylate	C₂₆H₄₆N₂O₆	详情	详情
(XXII)	55154	(2R,4S,5R)-5-[(1R,2S)-1-(acetylamino)-2-methoxy-2-methylpentyl]-4-[(Z)-1-propenyl]-2-pyrrolidinecarboxylic acid	C₁₇H₃₀N₂O₄	详情	详情
(XXIII)	55166	ethyl (2R,4S,5R)-5-[(1R,2S)-1-(acetylamino)-2-methoxy-2-methylpentyl]-4-[(Z)-1-propenyl]-2-pyrrolidinecarboxylate	C₁₉H₃₄N₂O₄	详情	详情

Extended Information