Methanol → 2-[4'-(2,8-Bis-trifluoromethyl-quinolin-4-yloxymethyl)-biphenyl-4-sulfonylamino]-3-methyl-butyric acid

HRID 133409Notes

Reaction equation

HRID 133409 reaction equation
C[O:2][C:3](=[O:44])[CH:4]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][O:25][C:26]3[C:35]4[C:30](=[C:31]([C:36]([F:39])([F:38])[F:37])[CH:32]=[CH:33][CH:34]=4)[N:29]=[C:28]([C:40]([F:43])([F:42])[F:41])[CH:27]=3)=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)(=[O:11])=[O:10])[CH:5]([CH3:7])[CH3:6].CO.[OH-].[Na+]>C1COCC1>[F:43][C:40]([F:41])([F:42])[C:28]1[CH:27]=[C:26]([O:25][CH2:24][C:21]2[CH:22]=[CH:23][C:18]([C:15]3[CH:14]=[CH:13][C:12]([S:9]([NH:8][CH:4]([CH:5]([CH3:7])[CH3:6])[C:3]([OH:44])=[O:2])(=[O:11])=[O:10])=[CH:17][CH:16]=3)=[CH:19][CH:20]=2)[C:35]2[C:30](=[C:31]([C:36]([F:37])([F:38])[F:39])[CH:32]=[CH:33][CH:34]=2)[N:29]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 865986322-[4'-(2,8-Bis-trifluoromethyl-quinolin-4-yloxymethyl)-biphenyl-4-sulfonylamino]-3-methyl-butyric acid methyl ester

Product 1

HCID 730444322-[4'-(2,8-Bis-trifluoromethyl-quinolin-4-yloxymethyl)-biphenyl-4-sulfonylamino]-3-methyl-butyric acidYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[4′-(2,8-Bis-trifluoromethyl-quinolin-4-yloxymethyl)-biphenyl-4-sulfonylamino]-3-methyl-butyric acid methyl ester (1.026 g, 1.6 mmol, 1 equiv.) was dissolved in THF (15 mL) and MeOH (6 mL) and 1N NaOH (17.6 mL, 11 equiv.) was added. The reaction was monitored by TLC. It was complete in 3 days. Solvent was removed by rotovap and the residue was dissolved in H2O. The mixture was then acidified to pH 3 with 1N HCl. The resulting precipitate was collected by filtration and washed with cold water and dried overnight. 460 mg of white solid was obtained in 46% yield.

Workup

  1. customSolvent was removed by rotovap
  2. dissolutionthe residue was dissolved in H2O
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with cold water
  5. customdried overnight

Sources & evidence

ORD record
ord-647bea4566b847dd927c5d799e30f440
Source dataset
uspto-grants-2008_06
Patent number
US07390833B2

Reaction notes

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