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

HRID 396115Notes

Reaction equation

HRID 396115 reaction equation
[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]

Participants

6

Reactant 4

HCID 962WaterHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 516920Potassium bisulfate2×HCID 21226445Aluminium lithium hydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

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/mmnol 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.

Workup

  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

Sources & evidence

ORD record
ord-31cc8d91fbfb4ab7a9b136af864b1a7b
Source dataset
uspto-grants-2003_08
Patent number
US06608030B1

Reaction notes

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