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

HRID 1589887Notes

Reaction equation

HRID 1589887 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. customat 0° C.
  2. customThe reaction immediately turned bright yellow
  3. washwashed with 10% sodium carbonate (1×50 ml), brine (2×50 ml)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationFiltration and evaporation
  6. customgave a white residue which
  7. customwas crystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-6674721813734e5f8575cdeb476e911b
Source dataset
uspto-grants-1993_04
Patent number
US05200412

Reaction notes

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