Potassium Carbonate → 3-[(3,4-Dichlorobenzyl)-methoxy-carbamoyl]-2-hydroxy-acrylic acid methyl ester

HRID 2214679Notes

Reaction equation

HRID 2214679 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:5][N:6]([O:18][CH3:19])[C:7](=[O:17])[CH:8]=[C:9]1[C:13](=[O:14])[O:12][C:11](C)(C)[O:10]1.C(=O)([O-])[O-].[K+].[K+]>CO.CCOC(C)=O>[CH3:11][O:12][C:13](=[O:14])[C:9]([OH:10])=[CH:8][C:7](=[O:17])[N:6]([CH2:5][C:4]1[CH:20]=[CH:21][C:22]([Cl:23])=[C:2]([Cl:1])[CH:3]=1)[O:18][CH3:19]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 85435466N-(3,4-Dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolane-4-ylidene)-N-methoxy-acetamide

Product 1

HCID 723950783-[(3,4-Dichlorobenzyl)-methoxy-carbamoyl]-2-hydroxy-acrylic acid methyl esterYield 33.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(3,4-dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolane-4-ylidene)-N-methoxy-acetamide (1.0 g, 2.8 mmol) and potassium carbonate (0.39 g, 2.8 mmol) in MeOH (20 mL) was stirred at room temp for 1 h. The suspension was diluted with EtOAc and washed with 1N HCl followed by brine. The organic phase was dried (sodium sulfate) and concentrated. The title compound was purified by flash chromatography eluting with 100% hexane followed by 25% EtOAc/hexane to give a white solid (0.3107 g, 33% yield). 1HNMR (300 MHz, CDCl3) δ: 13.28 (1H, s), 7.41 (2H, m), 7.15 (1H, dd, J=9.52, 1.47 Hz), 6.45 (1H, s), 4.77 (2H, s), 3.89 (3H, s), 3.72 (3H, s).

Workup

  1. washwashed with 1N HCl
  2. dry with materialThe organic phase was dried (sodium sulfate)
  3. concentrationconcentrated
  4. customThe title compound was purified by flash chromatography
  5. washeluting with 100% hexane

Sources & evidence

ORD record
ord-dec57398771a44548c0379644e4d3dff
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

Loading…