Sodium Hydroxide → HCID 86669791, compound

HRID 2371299Notes

Reaction equation

HRID 2371299 reaction equation
C[O:2][C:3](=[O:42])[CH:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]1([C:24](=[O:41])[N:25]([C:32]1[O:40][C:36]2=[CH:37][CH:38]=[CH:39][C:35]2=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]=[CH:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:14][CH:13]=1.[OH-].[Na+]>CCO.C1COCC1.O>[O:40]1[C:36]2=[CH:37][CH:38]=[CH:39][C:35]2=[CH:34][CH:33]=[C:32]1[N:25]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:24]([C:5]1([CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([CH:18]=[CH:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[CH:16][CH:17]=2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:4]1[C:3]([OH:42])=[O:2])=[O:41]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86669792HCID 86669792, compound

Product 1

HCID 86669791HCID 86669791, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

To a stirred solution of (R)-4-[2-(4-Benzofuran-2-yl-phenylcarbamoyl)-2-[4-(3,3-dimethyl-but-1-enyl)-phenyl-ethyl]-benzoic acid methyl ester (0.29 g, 0.52 mmol) in EtOH/THF/H2O (4:2:1) (12 mL) at rt, was added aq. 40% NaOH (2.5 ml), The reaction mixture was stirred for overnight, After completion of the reaction, the solvent was removed under reduced pressure. The crude was taken to pH=2 with 4N HCl and the resulting mixture was extracted with ethyl acetate. The organic layer was dried over MgSO4 and concentrated, the resulting compound was dried under vacuum to afford 4-[2-(4-Benzofuran-2-yl-phenylcarbamoyl)-2-[4-(3,3-dimethyl-but-1-enyl)-phenyl-ethyl]-benzoic acid as a solid (0.27 g, 98%):

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was removed under reduced pressure
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customthe resulting compound was dried under vacuum

Sources & evidence

ORD record
ord-5cf36902ff824b788e2eb4db40eb8fe2
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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