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

HRID 1006084ノート

反応式

HRID 1006084 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a5860a393df543f5b9d1d59b4af726af
出典データセット
uspto-grants-2004_09
特許番号
US06787559B2

反応ノート

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