Benzyl bromoacetate → HCID 20243506, compound

HRID 482934Notes

Reaction equation

HRID 482934 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].Br[CH2:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]>CCOCC>[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH:5][CH2:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]

Participants

4

Reactant 2

HCID 62576Benzyl bromoacetateHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 20243506HCID 20243506, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of aminoacetaldehyde dimethyl acetal (2.2 ml, 0.04 mole) in ether (10 ml) was cooled to 0° C. Benzyl bromoacetate (1.6 ml, 0.02 mole) was added. After stirring at ambient temperature overnight, the solid aminoacetaldehyde dimethyl acetal hydrobromide was filtered and the solution was concentrated to an oil. Flash chromatography on silica (LPS-1) (40:60 ethyl acetate:hexane eluant) gave 2.2 gms of the purified title compound.

Workup

  1. filtrationthe solid aminoacetaldehyde dimethyl acetal hydrobromide was filtered
  2. concentrationthe solution was concentrated to an oil
  3. customFlash chromatography on silica (LPS-1) (40:60 ethyl acetate:hexane eluant) gave 2.2 gms of the
  4. custompurified title compound

Sources & evidence

ORD record
ord-66ca136134b14dedadc124de9deca984
Source dataset
uspto-grants-1986_03
Patent number
US04576749

Reaction notes

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