Triphenylphosphine → 1,1-Dimethylethyl (2S)-4-bromo-2-[[(1,1-dimethylethoxy)carbonyl]amino]butanoate

HRID 591272노트

반응식

HRID 591272 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][CH2:11]O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:20]N1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:20][CH2:11][CH2:10][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 11054918(S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate

생성물 1

HCID 141930431,1-Dimethylethyl (2S)-4-bromo-2-[[(1,1-dimethylethoxy)carbonyl]amino]butanoate수율 41.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 5.00 g (18.2 mmol) tert-butyl N-(tert-butoxycarbonyl)-L-homoserinate (prepared according to J. Org. Chem. 1988, 53, 1900-1903), 3.23 g N-bromo succinimide (18.2 mmol), and 6.16 g polymer bound triphenylphosphine (loading approx. 3 mmol/g, approx. 18.5 mmol) in dichloromethane (60 mL) was stirred overnight at room temperature. All solids were removed by filtration, and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel (2.5→25% ethyl acetate in hexane) to give 2.56 g of the title compound (38% yield).

후처리

  1. customAll solids were removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (2.5→25% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-7ae8e20f92f84cd8af7a282740be61bd
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238631B2

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