Water → HCID 25007800, compound

HRID 1160514Notes

Reaction equation

HRID 1160514 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:39])[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]([S:18][CH2:19][CH2:20][CH3:21])=[C:16]([C:22](=[O:38])[NH:23][CH:24]3[CH:31]4[CH2:32][CH:27]5[CH2:28][C:29]([S:34]([CH3:37])(=[O:36])=[O:35])([CH2:33][CH:25]3[CH2:26]5)[CH2:30]4)[CH:15]=[N:14]2)=[CH:9][CH:8]=1.O>CO>[CH3:37][S:34]([C:29]12[CH2:33][CH:25]3[CH2:26][CH:27]([CH2:32][CH:31]([CH:24]3[NH:23][C:22]([C:16]3[CH:15]=[N:14][N:13]([C:10]4[CH:9]=[CH:8][C:7]([C:6]([OH:39])=[O:5])=[CH:12][CH:11]=4)[C:17]=3[S:18][CH2:19][CH2:20][CH3:21])=[O:38])[CH2:30]1)[CH2:28]2)(=[O:35])=[O:36]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 59516063HCID 59516063, compound

Product 1

HCID 25007800HCID 25007800, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Lithium hydroxide monohydrate (27.5 mg, 0.65 mmol) was added to a suspension of 4-[4-(5-Methanesulfonyl-adamantan-2-ylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]-benzoic acid methyl ester (Intermediate#105) (116 mg, 0.22 mmol) in methanol (4 mL)/water (2 mL) at ambient temperature. The resulting suspension was stirred at ambient temperature for 18 hours. The bulk of the organic solvent was removed in vacuo and the resulting solution was diluted with water (10 mL) and washed with ether (10 mL). The aqueous layer was acidified to ˜pH4 with 2M HCl then extracted with EtOAc (3×25 ml). The EtOAc layers were combined, washed sequentially with water (5 mL) and saturated brine (10 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford 4-[4-(5-Methanesulfonyl-adamantan-2-ylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]-benzoic acid (113 mg, 100%) as a white solid.

Workup

  1. customThe bulk of the organic solvent was removed in vacuo
  2. additionthe resulting solution was diluted with water (10 mL)
  3. washwashed with ether (10 mL)
  4. extractionthen extracted with EtOAc (3×25 ml)
  5. washwashed sequentially with water (5 mL) and saturated brine (10 mL)
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-9acb5a6e10324f9c9eb022ac94dc20db
Source dataset
uspto-grants-2010_10
Patent number
US07816391B2

Reaction notes

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