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【结 构 式】

【分子编号】44108

【品名】tert-butyl 3-nitropropanoate

【CA登记号】

【 分 子 式 】C7H13NO4

【 分 子 量 】175.18456

【元素组成】C 47.99% H 7.48% N 8% O 36.53%

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:(III)

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.

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