Triethylamine → (S)-N-CBZ-valinol

HRID 53113

反応式

HRID 53113 の反応式
[NH2:1][C@H:2]([CH2:6][OH:7])[CH:3]([CH3:5])[CH3:4].C(N(CC)CC)C.Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>C(Cl)Cl>[CH2:19]([O:18][C:16]([NH:1][C@H:2]([CH2:6][OH:7])[CH:3]([CH3:5])[CH3:4])=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 640993L-Valinol

生成物 1

HCID 10900657(S)-N-CBZ-valinol収率 95.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred solution of valinol (13.96 g, 0.14 mol) and triethylamine (18.87 mL, 0.14 mol) in 250 mL of dry methylene chloride cooled to 0° C. under a nitrogen atmosphere was added 19.3 mL (0.14 mol) of benzyl chloroformate dropwise over 20 min. After warming to RT overnight, the mixture was diluted with methylene chloride (100 mL) and washed with 1N HCl (2×), brine and dried with anhydrous magnesium sulfate. The resulting mixture was filtered and evaporated to give 30.70 g (95.6%) of N-benzyloxycarbonyl-valinol as a white solid: Rf =0.27 (silica gel; 1:1 hexane:ethyl acetate). Used without further purification.

後処理

  1. washwashed with 1N HCl (2×), brine
  2. dry with materialdried with anhydrous magnesium sulfate
  3. filtrationThe resulting mixture was filtered
  4. customevaporated

出典と根拠

ORDレコード
ord-07d3e2fb476846c98aa15dff4b0ec5d4
出典データセット
uspto-grants-1997_04
特許番号
US05618792

関連ノート

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