Phosgene → Methyl 2-isocyano-3-phenylpropanoate

HRID 1974013Notes

Reaction equation

HRID 1974013 reaction equation
C(Cl)(Cl)=O.[CH3:5][O:6][C:7](=[O:19])[C@H:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[NH:9][CH:10]=O.CN1CCOCC1>C(Cl)Cl>[CH3:5][O:6][C:7](=[O:19])[CH:8]([N+:9]#[C-:10])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 79724-MethylmorpholineHCID 7016392N-formylphenylalanine methyl ester

Product 1

HCID 2734779Methyl 2-isocyano-3-phenylpropanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of phosgene (5.2 g, 0.052 mole) in dry methylene chloride (45 ml) is added dropwise to a stirred solution of N-formylphenylalanine methyl ester (10.0 g, 0.048 mole) and 1-methylmorpholine (13 g, 0.125 mole) in dry methylene chloride (25 ml) at -30° C. After completion of the addition the filtrate is concentrated under reduced pressure at room temperature. Benzene is added to the residue followed by filtration and concentration of the resulting solution. The residue is distilled to afford the title compound as a yellow oil, b.p. 97° C/0.3 mm, νmaxCHCl3 2150, 1746, 1595, 1578, 1489, 694 cm-1.

Workup

  1. additionAfter completion of the addition the filtrate
  2. concentrationis concentrated under reduced pressure at room temperature
  3. additionBenzene is added to the residue
  4. filtrationfollowed by filtration and concentration of the resulting solution
  5. distillationThe residue is distilled

Sources & evidence

ORD record
ord-700f229736794de7af45c62563758350
Source dataset
uspto-grants-1976_12
Patent number
US04000122

Reaction notes

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