Sodium Hydroxide → HCID 15605608, compound

HRID 1994172Notes

Reaction equation

HRID 1994172 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[S:19][CH:20]=[CH:21][C:22]=3[NH:23][S:24]([CH:27]([CH3:29])[CH3:28])(=[O:26])=[O:25])=[CH:14][CH:13]=2)=[C:8]([O:30][CH2:31][CH3:32])[CH:7]=1)=[O:5])C.[OH-].[Na+]>C(O)C.O>[CH2:31]([O:30][C:8]1[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[CH:11]=[CH:10][C:9]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[S:19][CH:20]=[CH:21][C:22]=2[NH:23][S:24]([CH:27]([CH3:28])[CH3:29])(=[O:26])=[O:25])=[CH:14][CH:13]=1)[CH3:32]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58769100HCID 58769100, compound

Product 1

HCID 15605608HCID 15605608, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

The resultant ester may be hydrolyzed in the following manner: Mix 2-ethoxy-4′-[3-(propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-4-carboxylic acid ethyl ester (38 g, 80 mmol), in ethanol (100 mL) and NaOH 2 M in water (400 mL) and stir the reaction mixture for one hour at RT. Evaporate the ethanol and wash the aqueous mixture with 200 mL of EtOAc. Acidify the aqueous mixture to pH 2 using HCl 1N. Extract the desired product with EtOAc. Dissolve the crude in warmed acetone (500 ml) and add water (600 ml), maintaining the temperature at 55° C. Stir the mixture at 60° C. for 1 hour and then to RT. overnight. Filtrate the precipitate and dry under vacuum at 45° C. overnight. Yield 28 g, 78%. 1H NMR (300 MHz, DMSO): δ 1.14 (d, J=7.0 Hz, 6H), 1.31 (t, J=7.0 Hz, 3H), 3.06 (sept, J=7.0 Hz, 1H), 4.13 (q, J=7.0 Hz, 2H), 7.10 (d, J=5.3 Hz, 1H), 7.48 (d, J=7.6 Hz, 1H), 7.54 (d, J=5.3 Hz, 1H), 7.58-7.68 (m,4H), 7.72 (d, J=8.4 Hz, 2H), 9.22 (bs, 1H), 13.04 (bs, 1H).

Workup

  1. customEvaporate the ethanol
  2. washwash the aqueous mixture with 200 mL of EtOAc
  3. extractionExtract the desired product with EtOAc
  4. dissolutionDissolve the crude in warmed acetone (500 ml)
  5. additionadd water (600 ml)
  6. customto RT
  7. customovernight
  8. customFiltrate the precipitate and dry under vacuum at 45° C. overnight

Sources & evidence

ORD record
ord-921d92090e3e476a8f4fa42ea4f9aba9
Source dataset
uspto-grants-2010_01
Patent number
US07652064B2

Reaction notes

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