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

HRID 591277ノート

反応式

HRID 591277 の反応式
[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]

参加物

5

反応物 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 14037611n-Boc-d-homoserine tert-butyl ester

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-226d3170cc1549599a50f5c8abd84f95
出典データセット
uspto-grants-2016_01
特許番号
US09238631B2

反応ノート

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