Methanol → 3-{4-Fluoro-3-[(5-phenyl-furan-2-carbonyl)-amino]-phenyl}-acrylic acid

HRID 659120

Reaction equation

HRID 659120 reaction equation
C[O:2][C:3](=[O:27])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([NH:13][C:14]([C:16]2[O:17][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:19][CH:20]=2)=[O:15])[CH:7]=1.CO.[OH-].[Na+]>C1COCC1>[F:12][C:9]1[CH:10]=[CH:11][C:6]([CH:5]=[CH:4][C:3]([OH:27])=[O:2])=[CH:7][C:8]=1[NH:13][C:14]([C:16]1[O:17][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:19][CH:20]=1)=[O:15]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 684122363-{4-Fluoro-3-[(5-phenyl-furan-2-carbonyl)-amino]-phenyl}-acrylic acid methyl ester

Product 1

HCID 684127603-{4-Fluoro-3-[(5-phenyl-furan-2-carbonyl)-amino]-phenyl}-acrylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The ester (44) (18 mg, 0.049 mmol) was hydrolysed using Method C, except that MeOH (1 mL), THF (1 mL) and 1M NaOH (2 mL) were used, and the reaction was stirred for 1 hour. Yield: 3 mg, 17%; LC-MS tr 1.44 min; HPLC Purity: 91%; MS (ES+) m/z 352 (M+H); 1H NMR (400 MHz; MeOH): δ 6.50 (d, 1H), 7.05 (d, 1H), 7.25-7.60 (m, 6H), 7.70 (d, 1H), 7.95 (d, 2H), 8.15 (d, 1H)

Workup

  1. waitLC-MS tr 1.44 min

Sources & evidence

ORD record
ord-be8d23f51de04fc29322ac802b50f3e7
Source dataset
uspto-grants-2011_12
Patent number
US08080567B2

Linked notes

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