Methyl chloroacetate → N-(3,5-difluorobenzyl)-glycine methyl ester

HRID 1762798Notes

Reaction equation

HRID 1762798 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH2:5][NH2:6].Cl[CH2:12][C:13]([O:15][CH3:16])=[O:14].C(N(CC)CC)C>CN(C)C=O.CCOCC>[CH3:16][O:15][C:13](=[O:14])[CH2:12][NH:6][CH2:5][C:4]1[CH:3]=[C:2]([F:1])[CH:9]=[C:8]([F:10])[CH:7]=1

Participants

6

Reactant 3

HCID 7295Methyl chloroacetateHCID 8471TriethylamineHCID 1452113,5-Difluorobenzylamine

Product 1

HCID 14479943N-(3,5-difluorobenzyl)-glycine methyl esterYield 41%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3,5-difluorobenzylamine (12.3 g, 0.0863 mole), methyl chloroacetate (7.6 ml, 0.0863 mole) and triethylamine (12.0 ml, 0.0863 mole) in dry dimethylformamide (85 ml) was heated at 60° C. for 3 hours. The mixture was diluted with an equal volume of ether and the triethylamine hydrochloride filtered. The filtrate was concentrated under vacuum and the resultant oil triturated with ethyl acetate and the solution decanted from a small amount of residual oil. The solvent was removed and the product was purified by flash chromatography (silica) by eluting with hexane-ethyl acetate (70:30) to give an oil (7.61 g, 41%).

Workup

  1. filtrationthe triethylamine hydrochloride filtered
  2. concentrationThe filtrate was concentrated under vacuum
  3. customthe resultant oil triturated with ethyl acetate
  4. customthe solution decanted from a small amount of residual oil
  5. customThe solvent was removed
  6. customthe product was purified by flash chromatography (silica)
  7. washby eluting with hexane-ethyl acetate (70:30)

Sources & evidence

ORD record
ord-dce0212786ca4a2fb5eabe74813614a7
Source dataset
uspto-grants-1989_05
Patent number
US04835154

Reaction notes

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