Water → tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamate

HRID 32294

반응식

HRID 32294 반응식
[C:1]([NH:8][C@H:9]([C:14](O)=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].OS([O-])(=O)=O.[K+].O>CCOCC>[C:1]([NH:8][C@H:9]([CH:14]=[O:15])[CH2:10][CH:11]([CH3:12])[CH3:13])([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 516920Potassium bisulfate2회HCID 21226445Aluminium lithium hydride

생성물 1

HCID 104275tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamate

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

The Weinreb amide of BocLeucine was dissolved in dry Et2O and added by cannula to an Et2O suspension of an equimolar amount of LiAlH4 at 0° C. After stirring for one hour, the reaction flask was removed from 0° C. and allowed to warm to room temperature. After a reaction time of 80 minutes, an aqueous solution of KHSO4, (2 equiv. of KHSO4, 5 ml H2O/mmol of Weinreb amide) was added slowly while stirring. The aqueous phase was extracted with Et2O and the confined Et2O phases were washed with 3N HCl, saturated NaHCO3, and saturated NaCl. After drying (MgSO4,) and rotary evaporation, the oil was found to contain one compound by thin layer chromatography.

후처리

  1. customthe reaction flask was removed from 0° C.
  2. stirringwhile stirring
  3. extractionThe aqueous phase was extracted with Et2O
  4. washthe confined Et2O phases were washed with 3N HCl, saturated NaHCO3, and saturated NaCl
  5. customAfter drying
  6. custom(MgSO4,) and rotary evaporation

출처 및 근거

ORD 기록
ord-3c5c784040a64c87816d4340cee56144
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427591B2

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