Methyl iodide → (S)-Methyl 2-N-Cbz-3-N-Boc-propanoate

HRID 1934683Notes

Reaction equation

HRID 1934683 reaction equation
IC.[CH2:3]([O:10][C:11]([NH:13][C@@H:14]([CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:15]([OH:17])=[O:16])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:27](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:3]([O:10][C:11]([NH:13][C@@H:14]([CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:15]([O:17][CH3:27])=[O:16])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2756240L-N-Cbz-3-N-Boc-Amino-alanine

Product 1

HCID 10831821(S)-Methyl 2-N-Cbz-3-N-Boc-propanoateYield 104.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodomethane (554 mg) was added to a suspension of (S)-2-(benzyloxycarbonylamino)-3-(tert-butoxycarbonylamino)propionoic acid (1.1 g) and potassium carbonate (539 mg) in N,N-dimethylformamide (7 mL). The mixture was stirred for 2 hours at ambient temperature and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo to give methyl (S)-2-(benzyloxycarbonylamino)-3-(tert-butoxycarbonylamino)propionate (1.2 g) as an oil.

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-147f9dac545f4dd5b5e126346e0bc979
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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