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

HRID 1360166노트

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HRID 1360166 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 168478Rhodium acetate촉매HCID 63651,1-Dichloroethane용매

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온도
80 °C

실험 절차

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%.

후처리

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

출처 및 근거

ORD 기록
ord-cb3a68af140f42c8a17e551722efc526
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879848B2

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