Sodium Methoxide → 3-[(4-Fluoro-benzyl)-methoxy-carbamoyl]-2-hydroxy-acrylic acid methyl ester

HRID 2214544Notes

Reaction equation

HRID 2214544 reaction equation
C[C:2]1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[O:11][CH3:12])=[O:9])[C:4](=[O:21])[O:3]1.C[O-].[Na+]>CO>[CH3:2][O:3][C:4](=[O:21])[C:5]([OH:6])=[CH:7][C:8](=[O:9])[N:10]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=1)[O:11][CH3:12]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 730332332-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-benzyl)-N-methoxy-acetamide

Product 1

HCID 723950773-[(4-Fluoro-benzyl)-methoxy-carbamoyl]-2-hydroxy-acrylic acid methyl esterYield 95.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluorobenzyl)-N-methoxy-acetamide (0.64 g, 2.07 mmol) in methanol (50 ml), was treated at 22° C. with 0.025 ml of a 4.6 M solution of sodium methoxide in methanol and the resulting mixture was stirred for 2 h at the same temperature. The reaction mixture was then quenched by the addition of 1 ml of 1 N hydrochloric acid and the solvent was concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed with water and brine and then dried over anhydrous magnesium sulfate. Evaporation of the solvent and crystallization of the residue from a mixture of ethyl acetate and hexane gave 0.559 g (95% yield) of the title ester as white prisms; mp 71° C. 1HNMR 400 MHz (CDCl3) δ (ppm), mixture of rotamers, major: 3.69 (3H, s, OCH3), 3.89 (3H, s, OCH3), 4.80 (2H, s, NCH2), 6.45 (1H, s, CH), 7.03 (2H, m, aromatics), 7.30 (2H, m, aromatics). Anal. calcd for C13H14FNO5: C, 55.12; H, 4.98; N, 4.94. Found: C, 54.95; H, 4.73; N, 4.67.

Workup

  1. customThe reaction mixture was then quenched by the addition of 1 ml of 1 N hydrochloric acid
  2. concentrationthe solvent was concentrated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customEvaporation of the solvent and crystallization of the residue
  7. additionfrom a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-9664e220ac2a463e887727de2fbc0363
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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