Methylamine → Benzyl N-[(1S)-1-(methylcarbamoyl)-2-phenylethyl]carbamate

HRID 327792Notes

Reaction equation

HRID 327792 reaction equation
[N+](C1C=CC(O[C:11](=[O:31])[C@H:12]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[NH:13][C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])=CC=1)([O-])=O.[CH3:32][NH2:33]>C(Cl)Cl.C(O)C>[CH3:32][NH:33][C:11](=[O:31])[C@H:12]([CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[NH:13][C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 151025Z-Phe-ONp

Product 1

HCID 13443905Benzyl N-[(1S)-1-(methylcarbamoyl)-2-phenylethyl]carbamateYield 81%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of N-benzyloxycarbonyl-L-phenylalanine p-nitrophenyl ester (5.0 g, 11.9 mmol) in DCM at 0° C. was slowly added a solution of 8M methylamine (1.5 ml, 11.9 mmol) in ethanol. The reaction immediately turned bright yellow and was stirred for 0.5 h. The reaction was diluted with DCM (50 ml), washed with 10% sodium carbonate (1×50 ml), brine (2×50 ml) and dried over anhydrous magnesium sulphate. Filtration and evaporation gave a white residue which was crystallised from ethyl acetate/hexane to give N-benzyloxycarbonyl-L-phenylalanine methylamide (3.0 g, 81%) as a white crystalline solid.

Workup

  1. customThe reaction immediately turned bright yellow
  2. washwashed with 10% sodium carbonate (1×50 ml), brine (2×50 ml)
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationFiltration and evaporation
  5. customgave a white residue which
  6. customwas crystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-0d537814ed5342b9a422b627093bed42
Source dataset
uspto-grants-1993_12
Patent number
US05274094

Reaction notes

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