Benzene → N-chloroformyl,N-phenyl valine

HRID 1389361Notes

Reaction equation

HRID 1389361 reaction equation
[C:1]1([NH:7][C@H:8]([C:12]([OH:14])=[O:13])[CH:9]([CH3:11])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15](Cl)([Cl:17])=[O:16].C1C=CC=CC=1.CN(C1C=CC=CN=1)C>C(Cl)(Cl)Cl.O>[Cl:17][C:15]([N:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C@H:8]([C:12]([OH:14])=[O:13])[CH:9]([CH3:11])[CH3:10])=[O:16]

Participants

6

Reactant 4

HCID 241Benzene2×HCID 6371Phosgene2×HCID 218852-Dimethylaminopyridine2×HCID 10867191N-phenylvaline

Product 1

HCID 86737428N-chloroformyl,N-phenyl valine

Reagents, catalysts & solvents 1

HCID 22418719Chloroform waterSolvent

Procedure

To the m-phenoxybenzyl ester of N-phenyl valine (1.2 mmole) is added 12.5% phosgene in benzene (2.3 mmole), cooled in an ice bath, and then dimethylaminopyridine (1.22 mmole). The reaction mixture is stirred at RT for 3 days. Then one ml of benzene, 0.15 g of dimethylaminopyridine and 2 ml of phosgene are added and the reaction stirred overnight at RT. The reaction is worked up using chloroform/water. The chloroform layer is washed with dilute sulfuric acid, water and brine, dried over sodium sulfate and filtered. The solvent is removed by rotoevaporation to yield the m-phenoxybenzyl ester of N-chloroformyl,N-phenyl valine.

Workup

  1. temperaturecooled in an ice bath
  2. stirringthe reaction stirred overnight at RT
  3. washThe chloroform layer is washed with dilute sulfuric acid, water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customThe solvent is removed by rotoevaporation

Sources & evidence

ORD record
ord-ad90cdaddf5d4c1abb8ff1cbbf7007ae
Source dataset
uspto-grants-1981_01
Patent number
US04243819

Reaction notes

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