Potassium Hydroxide → erythro-N-Boc-D-phenylalanine epoxide

HRID 424978

反応式

HRID 424978 の反応式
[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C@@H:9]([OH:12])[CH2:10]Cl)([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>C(O)C>[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]([C@@H:9]1[CH2:10][O:12]1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 60170213HCID 60170213、化合物

生成物 1

HCID 11357515erythro-N-Boc-D-phenylalanine epoxide収率 69.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a stirred solution of (R,R)-1-benzyl-3-chloro-2-hydroxypropylcarbamic acid tert-butyl ester (4.45 g, 15 mmol) in ethanol (125 mL) at 0° C. is added KOH (0.5M in ethanol, 36 ml, 18 mmol). After stirring for 20 min, the mixture is concentrated under reduced pressure and the residue is dissolved in ethyl acetate, washed with saturated ammonium chloride (aq), water and then brine, dried over Na2SO4 and concentrated under reduced pressure. The resulting white solid is purified using General Purification Procedure E to afford the title compound as a white solid (2.7 g, 10.4 mmol).

後処理

  1. concentrationthe mixture is concentrated under reduced pressure
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. washwashed with saturated ammonium chloride (aq), water
  4. dry with materialbrine, dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting white solid is purified
  7. customGeneral Purification Procedure E

出典と根拠

ORDレコード
ord-2f53e88e4ec4460b9f8801f6c321376e
出典データセット
uspto-grants-2012_01
特許番号
US08106090B2

関連ノート

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