Triphenylphosphine → (R)-4-Bromo-2-[[(tert-butoxy)carbonyl]amino]butanoic acid tert-butyl ester

HRID 591277노트

반응식

HRID 591277 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 14037611n-Boc-d-homoserine tert-butyl ester

생성물 1

HCID 14193045(R)-4-Bromo-2-[[(tert-butoxy)carbonyl]amino]butanoic acid tert-butyl ester수율 34%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 1.39 g (5.05 mmol) tert-butyl N-(tert-butoxycarbonyl)-D-homoserinate (prepared according to J. Org. Chem. 1988, 53, 1900-1903), 899 mg N-bromo succinimide (5.05 mmol), and 1.68 g polymer bound triphenylphosphine (loading approx. 3 mmol/g, approx. 5.0 mmol) in dichloromethane (17 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 580 mg of the title compound (34% 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-226d3170cc1549599a50f5c8abd84f95
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238631B2

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