Benzyl chloroformate → 4-Methyl-N-((phenylmethoxy)carbonyl)-L-leucine

HRID 907614Notes

Reaction equation

HRID 907614 reaction equation
[OH-].[Na+].[NH2:3][C@@H:4]([CH2:8][C:9]([CH3:12])([CH3:11])[CH3:10])[C:5]([OH:7])=[O:6].[CH2:13]([O:20][C:21](Cl)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(#N)C>[CH2:13]([O:20][C:21]([NH:3][C@@H:4]([CH2:8][C:9]([CH3:12])([CH3:11])[CH3:10])[C:5]([OH:7])=[O:6])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 194032(2S)-2-Amino-4,4-dimethylpentanoic acid

Product 1

HCID 70202524-Methyl-N-((phenylmethoxy)carbonyl)-L-leucine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 1M solution of NaOH (135 ml, 135 mmol) was added 2(S)-amino-4,4-dimethylpentanoic acid (commercially available) (9.8 g, 67.5 mmol), followed by benzyloxycarbonyl chloride (11.6 ml, 80.99 mmol) in acetonitrile (20 ml) and the reaction mixture was stirred for 12 h at room temperature. The solvent was evaporated using rotavap and the slurry was washed with hexane and then adjusted the pH to 6 using 6N HCl. The resulting solution was extracted with ethyl acetate. The organic layer was washed with brine and dried over MgSO4. The solvent was evaporated to get 2(S)-benzyloxycarbonylamino-4,4-dimethylpentanoic acid (18.6 g) as a sticky gum which was used in the next step without further purification.

Workup

  1. customThe solvent was evaporated
  2. washthe slurry was washed with hexane
  3. extractionThe resulting solution was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-c92b337ac7e54067a8e69d9f0d0bd431
Source dataset
uspto-grants-2011_09
Patent number
US08013186B2

Reaction notes

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