Water → HCID 25007800, compound

HRID 1799379Notes

Reaction equation

HRID 1799379 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, compound2×

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 to 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 to brine (10 mL)
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-f4a8d11e870a4afb8578ed0962b1322c
Source dataset
uspto-grants-2013_01
Patent number
US08344016B2

Reaction notes

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