Benzyl Bromide → (R)-benzyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate

HRID 1760772노트

반응식

HRID 1760772 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]([OH:15])=[O:14])[CH:10]([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O>[CH2:22]([O:14][C:13](=[O:15])[C@@H:9]([CH:10]([CH3:11])[CH3:12])[NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 637605(2R)-2-(((tert-butoxy)carbonyl)amino)-3-methylbutanoic acid

생성물 1

HCID 11243734(R)-benzyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate수율 98.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

N-Tert-butoxycarbonyl-D-valine (70 g, 0.32 mol) and cesium carbonate (200.2 g, 0.615 mol) were stirred in dry dimethylformamide (550 mL). Benzyl bromide (40.32 mL, 0.336 mol) was added and the reaction mixture was stirred overnight. The material was concentrated on the roto-evaporator and the residue was dissolved in methylene chloride (200 mL) and the methylene chloride layer was washed with water and brine, dried over magnesium sulfate and concentrated to give N-tert-butoxycarbonyl-D-valine benzyl ester (97 g) as a viscous oil.

후처리

  1. concentrationThe material was concentrated on the roto-evaporator
  2. dissolutionthe residue was dissolved in methylene chloride (200 mL)
  3. washthe methylene chloride layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b43dccf219044a56b351c661f2c4de9e
출처 데이터셋
uspto-grants-2005_01
특허 번호
US06844366B2

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