Sodium Hydroxide → HCID 67487860, compound

HRID 2371248Notes

Reaction equation

HRID 2371248 reaction equation
C[O:2][C:3](=[O:42])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([C:24](=[O:41])[N:25]([C:32]2[O:40][C:36]3=[CH:37][CH:38]=[CH:39][C:35]3=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=3)=[CH:14][CH:13]=2)=[CH:6][CH:5]=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]([CH:11]([C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=2)=[CH:16][CH:17]=1)[CH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:42])=[O:2])=[CH:5][CH:6]=1)=[O:41]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68181142HCID 68181142, compound

Product 1

HCID 67487860HCID 67487860, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

To a stirred solution of 4-[2-(4-benzofuran-2-yl-phenylcarbamoyl)-2-(4-cyclohex-1-enyl-phenyl)-ethyl]-benzoic acid methylester (6) (0.42 g, 0.75 mmol) in EtOH/THF/H2O (4:2:1) (20 mL) at rt, was added aq. 40% NaOH (2.5 ml). The reaction mixture was stirred overnight. After completion of the reaction, the solvent was removed under reduced pressure and the crude was acidified with 4N HCl (pH=2). 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-2yl-phenylcarbamoyl)-2-(4-cyclohex-1-enyl-phenyl)-ethyl]-benzoic acid as a solid (0.35 g): 1H NMR (300 MHz, CD3OD): 10.23 (s, 1H), 7.78 (d, J=8.7 Hz, 4H), 7.55-7.66 (m, 4H), 7.20-7.40 (m, 9H), 6.10 (bt, 1H), 4.03 (t, J=7.2 Hz, 1H), 3.45 (dd, J=5.0, 9.0 Hz, 1H), 3.03 (dd, J=5.7, 12.9 Hz, 1H), 2.20-2.40 (m, 2H), 2.10-2.15 (m, 2H), 1.65-1.75 (m, 2H), 1.50-1.60 (m, 2H); LC-MS m/z=541 [C37H34NO3+H]+.

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-a28e1ae59a48454899dff1d7afe536f8
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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