Ethyl diazoacetate → (S)-(2-t-butoxycarbonylamino-1-methyl-ethoxy)-acetic acid ethyl ester

HRID 1360166ノート

反応式

HRID 1360166 の反応式
[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][C@@H:9]([OH:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].[N+](=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N-]>ClC(Cl)C.C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][O:11][C@@H:9]([CH3:10])[CH2:8][NH:7][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:12])[CH3:20]

参加物

5

反応物 2

HCID 12192Ethyl diazoacetateHCID 11789722N-Boc-(S)-1-amino-2-propanol

生成物 1

HCID 86621906(S)-(2-t-butoxycarbonylamino-1-methyl-ethoxy)-acetic acid ethyl ester収率 69.4%

試薬・触媒・溶媒 2

HCID 168478Rhodium acetate触媒HCID 63651,1-Dichloroethane溶媒

反応条件

温度
80 °C

実験手順

1.16 g (6.61 mmol) of (S)-(2-hydroxy-propyl)-carbamic acid t-butyl ester was dissolved in 20 mL of dichloroethane, then 0.66 mL (9.84 mmol) of ethyl diazoacetate was added thereto. 57 mg (0.12 mmol) of rhodium acetate was dropwise added thereto, and then heated to at 80° C. for 2 hour. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to give 1.2 g (4.59 mmol) of the title compound in a yield of 69%.

後処理

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-cb3a68af140f42c8a17e551722efc526
出典データセット
uspto-grants-2011_02
特許番号
US07879848B2

反応ノート

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