Benzyloxyacetyl chloride → HCID 22130044, compound
Reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].C(OCCC1N(CCC2C=CC=CC=2)C(SC2C=C(F)C=C(F)C=2)=C(C(C)C)N=1)(=O)N.[CH2:40]([O:47][CH2:48][C:49](Cl)=[O:50])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH:7][C:49](=[O:50])[CH2:48][O:47][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH3:3]Participants
Procedure
In 50 ml of methylene chloride was added 15.0 g (35.8 mmol) of glycine ethyl ester hydrochloric acid, followed by addition of 9.2 9 (75.3 mmol) of 4-dimethylaminopyridine under ice-cooling. After stirring for 10 minutes, 6.5 ml (39.4 mmol) of benzyloxyacetylchloride was added dropwise under ice-cooling over 30 minutes. The temperature was raised up to room temperature, and the mixture was stirred for 12 hours. To the mixture, 20 ml of methylene chloride was added, and filtered. To the filtrate, 5% hydrochloric acid was added, and the mixture was extracted with methylene chloride. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated and 9.0 g of N-benzyloxyacetylglycine ethyl ester was obtained (yield 100%).
Workup
- temperaturecooling
- temperaturecooling over 30 minutes
- stirringthe mixture was stirred for 12 hours
- filtrationfiltered
- additionTo the filtrate, 5% hydrochloric acid was added
- extractionthe mixture was extracted with methylene chloride
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated
Sources & evidence
- ORD record
- ord-ae2a925ee1e148f6b82fb8762d9e2ca1
- Source dataset
- uspto-grants-2000_11
- Patent number
- US06147097
Reaction notes
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