Water → HCID 25006311, compound

HRID 1799371Notes

Reaction equation

HRID 1799371 reaction equation
C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:15]([S:16][CH2:17][CH2:18][CH3:19])=[C:14]([C:20](=[O:28])[NH:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:13]=[N:12]2)=[CH:6][CH:5]=1.[Li+].[OH-].O>CO>[CH:22]1([NH:21][C:20]([C:14]2[CH:13]=[N:12][N:11]([CH2:10][C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:29])=[O:2])=[CH:5][CH:6]=3)[C:15]=2[S:16][CH2:17][CH2:18][CH3:19])=[O:28])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 59516094HCID 59516094, compound2×

Product 1

HCID 25006311HCID 25006311, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(4-Cyclohexylcarbamoyl-5-propylsulfanyl-pyrazol-1-ylmethyl)-benzoic acid methyl ester (116 mg, 0.28 mmol) (Intermediate #40) and LiOH (47 mg, 1.12 mmol) in MeOH (2 ml)/Water (1 ml) was stirred overnight at ambient temperature. The bulk of the MeOH was removed in vacuo and the resulting solution was treated with citric acid (˜10 ml) then extracted with EtOAc (2ט15 ml). The organic layers were combined, washed with brine (˜10 ml), dried (MgSO4), filtered and evaporated to yield the title compound as a white solid (102 mg, 91%).

Workup

  1. customThe bulk of the MeOH was removed in vacuo
  2. additionthe resulting solution was treated with citric acid (˜10 ml)
  3. extractionthen extracted with EtOAc (2ט15 ml)
  4. washwashed with brine (˜10 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-5bdb422c463d43c1a7d269a3caeffa41
Source dataset
uspto-grants-2013_01
Patent number
US08344016B2

Reaction notes

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