Hydrochloric Acid → 3-[(4-Fluoro-benzyl)-methoxy-carbamoyl]-2-hydroxy-acrylic acid

HRID 1836464

Reaction equation

HRID 1836464 reaction equation
CC1(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.[OH-].[Na+].Cl>O1CCCC1>[F:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:10]([O:11][CH3:12])[C:8]([CH:7]=[C:5]([OH:6])[C:4]([OH:21])=[O:3])=[O:9])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 730332332-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-benzyl)-N-methoxy-acetamide

Product 1

HCID 761794303-[(4-Fluoro-benzyl)-methoxy-carbamoyl]-2-hydroxy-acrylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-benzyl)-N-methoxy-acetamide (3.65 g, 11.8 mmol) in tetrahydrofuran (150 ml) was treated at 15° C. with 35 ml (35 mmol) of 1 M aqueous sodium hydroxide. After 30 minutes, the reaction mixture was acidified with 1N hydrochloric acid (65 ml) and extracted with ethyl acetate. The organic phase was washed with brine, dried (magnesium sulfate) and evaporated in vacuo to give a white solid. Recrystallization from ethyl acetate and hexane gave 3.04 g (96% yield) of the title material as white needles; mp 129° C. (dec.). 1HNMR 400 MHz (CDCl3) δ (ppm): 3.73 (3H, s), 4.84 (2H, s), 6.57 (1H, s), 7.07 (2H, mn), 7.34 (2H, m). 13CNMR (enol form) 125 MHz (DMSO-d6) δ (ppm): 47.08, 63.05, 93.35, 130.61, 130.83, 130.90, 132.86, 132.89, 133.14, 133.16, 161.02, 161.38, 163.32, 163.81, 170.97. Anal. calcd for C12H12FNO5: C, 53.53; H, 4.49; N, 5.20; Found: C, 53.78; H, 4.30; N, 4.90.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried (magnesium sulfate)
  4. customevaporated in vacuo
  5. customto give a white solid
  6. customRecrystallization from ethyl acetate and hexane

Sources & evidence

ORD record
ord-8b5ec6c7b3f14e7c927ded3eef64d733
Source dataset
uspto-grants-2004_08
Patent number
US06777440B2

Linked notes

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