tert-butyl 3-[((2S)-2-[[(benzyloxy)carbonyl]amino]-3-methylbutanoyl)amino]-5-fluoro-4-hydroxypentanoate -Drug Synthesis Database

【结构式】

【分子编号】44111

【品名】tert-butyl 3-[((2S)-2-[[(benzyloxy)carbonyl]amino]-3-methylbutanoyl)amino]-5-fluoro-4-hydroxypentanoate

【CA登记号】

【分子式】C₂₂H₃₃FN₂O₆

【分子量】440.5123032

【元素组成】C 59.99% H 7.55% F 4.31% N 6.36% O 21.79%

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：(VII)

2-Fluoroethanol (I) was oxidized under Swern conditions to afford 2-fluoroacetaldehyde (II), which was condensed with tert-butyl 3-nitropropionate (III), yielding the hydroxy ester (IV). Hydrogenation of the nitro group of (IV) over Raney nickel produced amine (V). Subsequent coupling of N-carbobenzoxy-L-valine (VI) with amine (V) in the presence of EDC and HOBt furnished amide (VII). The hydroxyl group of (VII) was then oxidized to the corresponding ketone (VIII) by using Dess-Martin periodinane. Finally, the tert-butyl ester was cleaved by treatment with trifluoroacetic acid.

参考文献中间体

合成目标

【1】 Guastella, J.; Yang, W.; Cai, S.X.; Keana, J.F.W.; Drewe, J.A. (Cytovia, Inc.); Dipeptide apoptosis inhibitors and the use thereof. EP 1033910; US 6184210; WO 9918781 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	44106	2-fluoro-1-ethanol	371-62-0	C₂H₅FO	详情	详情
(II)	44107	2-fluoroacetaldehyde		C₂H₃FO	详情	详情
(III)	44108	tert-butyl 3-nitropropanoate		C₇H₁₃NO₄	详情	详情
(IV)	44109	tert-butyl 5-fluoro-4-hydroxy-3-nitropentanoate		C₉H₁₆FNO₅	详情	详情
(V)	44110	tert-butyl 3-amino-5-fluoro-4-hydroxypentanoate		C₉H₁₈FNO₃	详情	详情
(VI)	18092	(2S)-2-[[(benzyloxy)carbonyl]amino]-3-methylbutyric acid		C₁₃H₁₇NO₄	详情	详情
(VII)	44111	tert-butyl 3-[((2S)-2-[[(benzyloxy)carbonyl]amino]-3-methylbutanoyl)amino]-5-fluoro-4-hydroxypentanoate		C₂₂H₃₃FN₂O₆	详情	详情
(VIII)	44112	tert-butyl 3-[((2S)-2-[[(benzyloxy)carbonyl]amino]-3-methylbutanoyl)amino]-5-fluoro-4-oxopentanoate		C₂₂H₃₁FN₂O₆	详情	详情

Extended Information