Water → methyl (2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoate

HRID 1859639Notes

Reaction equation

HRID 1859639 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:20]([OH:22])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23](=O)([O-])O.[K+].CI.O>CN(C=O)C>[CH3:23][O:21][C:20](=[O:22])[CH:12]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 100081N-benzyloxycarbonyl-DL-3-phenylalanineHCID 516893Potassium Bicarbonate

Product 1

HCID 11438389methyl (2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoateYield 101%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-benzyloxycarbonyl-DL-phenylalanine (155 g, 0.518 mol) in DMF (800 mL) were added mortar-pulverized potassium hydrogencarbonate (104 g, 1.04 mol) and methyl iodide (53 mL, 0.86 mol), and the mixture was stirred at room temperature for 5 hours. This reaction mixture was added to water (1800 mL) and extracted with ethyl acetate-hexane (4:1). The extract was washed successively with 2 portions of water (500 mL each), 5% sodium sulfite aqueous solution (500 ml) and saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give 164 g (100%) of N-benzyloxycarbonyl-DL-phenylalanine methyl ester as a colorless clear oil.

Workup

  1. extractionextracted with ethyl acetate-hexane (4:1)
  2. washThe extract was washed successively with 2 portions of water (500 mL each), 5% sodium sulfite aqueous solution (500 ml) and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3b64b3b89ca7460db05d0210f68263dd
Source dataset
uspto-grants-2003_03
Patent number
US06528514B1

Reaction notes

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