Water → Glycine, N-(2-chlorobenzoyl)-, methyl ester

HRID 1510274Notes

Reaction equation

HRID 1510274 reaction equation
[CH3:1][O:2][C:3](=[O:6])[CH2:4][NH2:5].C(N(CC)CC)C.[Cl:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](Cl)=[O:18].O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:6])[CH2:4][NH:5][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=1[Cl:14]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 691102-Chlorobenzoyl chlorideHCID 69221Glycine methyl ester

Product 1

HCID 531380Glycine, N-(2-chlorobenzoyl)-, methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Amino-acetic acid methyl ester (5 g, 40 mmol) was suspended in DMF and treated with triethylamine (13.9 mL, 100 mmol) and 2-chloro-benzoyl chloride (5 mL, 40 mmol). The reaction mixture was stirred at room temperature overnight. Water was added to the reaction, and the mixture was extracted with ethyl acetate three times. The organic layers were combined and dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography using ethyl acetate/hexane to yield (2-chloro-benzoylamino)-acetic acid methyl ester as a light yellow solid. LCMS calcd for C10H10ClNO3 (m/e) 227, obsd 228 (M+H).

Workup

  1. extractionthe mixture was extracted with ethyl acetate three times
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-53a208eea01f434eafce75080929e5d3
Source dataset
uspto-grants-2012_07
Patent number
US08211914B2

Reaction notes

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