Benzyl chloroformate → Glycine, N-[(phenylmethoxy)carbonyl]-N-(phenylmethyl)-
Reaction equation
Cl.[CH2:2]([NH:9][CH2:10][C:11]([OH:13])=[O:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+].Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>>[CH2:2]([N:9]([C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[CH2:10][C:11]([OH:13])=[O:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1Participants
Conditions
- Temperature
- -5 °C
Procedure
N-Benzylglycine hydrochloride was taken up in 2-N sodium hydroxide and the mixture was stirred at -5° C. while 4-N sodium hydroxide and benzyl chloroformate were simultaneously added dropwise. The mixture was stirred in the cold for 2 hours and then stirred at room temperature for 0.5 hour. Excess benzyl chloroformate was removed by extraction with ether. The aqueous layer was cooled to -5° C. and acidified with concentrated hydrochloric acid. The mixture was stirred in the cold for 1 hour, then brought to room temperature and extracted 4 times with diethyl ether. The diethyl ether extracts were back-washed with water, filtered and then dried over anhydrous sulphate and again filtered. Evaporation gave N-benzyl-N-benzyloxycarbonyl-glycine in the form of an oil.
Workup
- additionwere simultaneously added dropwise
- stirringstirred at room temperature for 0.5 hour
- customExcess benzyl chloroformate was removed by extraction with ether
- stirringThe mixture was stirred in the cold for 1 hour
- custombrought to room temperature
- extractionextracted 4 times with diethyl ether
- washThe diethyl ether extracts were back-washed with water
- filtrationfiltered
- dry with materialdried over anhydrous sulphate
- filtrationagain filtered
- customEvaporation
Sources & evidence
- ORD record
- ord-bb04fa50669d4fcb9cfd73860e76f148
- Source dataset
- uspto-grants-1981_02
- Patent number
- US04250085
Reaction notes
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