Benzyloxyacetyl chloride → HCID 22130044, compound

HRID 1416007Notes

Reaction equation

HRID 1416007 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].[CH2:9]([O:16][CH2:17][C:18](Cl)=[O:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH:7][C:18](=[O:19])[CH2:17][O:16][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:3]

Participants

5

Reactant 2

HCID 177085Benzyloxyacetyl chlorideHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 22130044HCID 22130044, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

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 g (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

  1. temperaturecooling
  2. temperaturecooling over 30 minutes
  3. stirringthe mixture was stirred for 12 hours
  4. filtrationfiltered
  5. additionTo the filtrate, 5% hydrochloric acid was added
  6. extractionthe mixture was extracted with methylene chloride
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9e2e105d18c04f54a7dacbde48becff1
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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