Sodium Hydroxide → 3-{3-[(5-Benzoyl-furan-2-carbonyl)-amino]-phenyl}-acrylic acid

HRID 659098Notes

Reaction equation

HRID 659098 reaction equation
C([O:3][C:4](=[O:29])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([C:16]2[O:17][C:18]([C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:19][CH:20]=2)=[O:15])[CH:8]=1)C.[OH-].[Na+]>CCO>[C:21]([C:18]1[O:17][C:16]([C:14]([NH:13][C:9]2[CH:8]=[C:7]([CH:6]=[CH:5][C:4]([OH:29])=[O:3])[CH:12]=[CH:11][CH:10]=2)=[O:15])=[CH:20][CH:19]=1)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 684126103-{3-[(5-Benzoyl-furan-2-carbonyl)-amino]-phenyl}-acrylic acid ethyl ester

Product 1

HCID 684135383-{3-[(5-Benzoyl-furan-2-carbonyl)-amino]-phenyl}-acrylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The ester (10) (28 mg, 0.072 mmol) was hydrolysed using Method C, except that EtOH (0.15 mL) and 1M NaOH (0.15 mL) were used. After the reaction, the solvent was removed under a stream of nitrogen gas and the residue acidified to pH 5 using 1N HCl. The precipitate was filtered off and dried to give the title compound. Yield: 8 mg, 31%; LC-MS tr 1.95 min; HPLC Purity: 98%; MS (ES+) m/z 362 (M+H); 1H NMR (400 MHz; DMSO): δ 6.4 (d, 1H), 7.10 (d, 1H), 7.20-7.40 (m, 2H), 7.55 (m, 1H), 7.60-7.80 (m, 3H), 7.80-7.90 (d, 1H), 7.95 (s, 1H), 7.95-8.10 (m, 3H)

Workup

  1. customAfter the reaction
  2. customthe solvent was removed under a stream of nitrogen gas
  3. filtrationThe precipitate was filtered off
  4. customdried

Sources & evidence

ORD record
ord-c3568bc12d1e4c58b1fe031ebfb593a8
Source dataset
uspto-grants-2011_12
Patent number
US08080567B2

Reaction notes

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