Gamma-Aminobutyric Acid → 4-{4-[(3,4-Dichloro-benzyl)-methoxy-carbamoyl]-3-hydroxy-2-oxo-2,5-dihydro-pyrrol-1-yl}-butyric acid

HRID 2214681Notes

Reaction equation

HRID 2214681 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH2:8]=O.CO[C:12](=[O:30])[C:13]([OH:29])=[CH:14][C:15](=[O:28])[N:16]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=1)[O:17][CH3:18]>C(O)(=O)C>[Cl:27][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][C:23]=1[Cl:26])[CH2:19][N:16]([O:17][CH3:18])[C:15]([C:14]1[CH2:8][N:1]([CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6])[C:12](=[O:30])[C:13]=1[OH:29])=[O:28]

Participants

5

Reactant 3

HCID 119Gamma-Aminobutyric AcidHCID 712FormaldehydeHCID 723950783-[(3,4-Dichlorobenzyl)-methoxy-carbamoyl]-2-hydroxy-acrylic acid methyl ester

Product 1

HCID 546917114-{4-[(3,4-Dichloro-benzyl)-methoxy-carbamoyl]-3-hydroxy-2-oxo-2,5-dihydro-pyrrol-1-yl}-butyric acidYield 34.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-amino butyric acid (0.093 g, 0.90 mmol) in acetic acid (0.5 mL) at 55° C. was added paraformaldehyde (0.027 g, 0.90 mmol). After stirring for 10 min, 3-[(3,4-dichloro-benzyl)-methoxy-carbamoyl]-2-hydroxy-acrylic acid methyl ester (0.2978 g, 0.89 mmol) was added and the mixture was stirred at 55° C. for 1 h. The clear yellow solution was cooled, concentrated and purified by preparative HPLC (C18, ODS-A, S-75 μm, 10%–40% acetonitrile/water/0.5% HCl) to give the title compound as a yellow foam (0.129 g, 34% yield). HRMS (M+H) calcd for C17H19N2Cl2O6: 417.06203; found: 417.0607.

Workup

  1. stirringthe mixture was stirred at 55° C. for 1 h
  2. temperatureThe clear yellow solution was cooled
  3. concentrationconcentrated
  4. custompurified by preparative HPLC (C18, ODS-A, S-75 μm, 10%–40% acetonitrile/water/0.5% HCl)

Sources & evidence

ORD record
ord-65db8c4d59a34bb5a573302ad8e12389
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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