Sodium Hydroxide → HCID 25006309, compound

HRID 1160505Notes

Reaction equation

HRID 1160505 reaction equation
[CH:1]1([NH:7][C:8]([C:10]2[CH:11]=[N:12][N:13]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][C:26]([O:28]C)=[O:27])=[CH:21][CH:20]=3)[C:14]=2[S:15][CH2:16][CH2:17][CH3:18])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([NH:7][C:8]([C:10]2[CH:11]=[N:12][N:13]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][C:26]([OH:28])=[O:27])=[CH:21][CH:20]=3)[C:14]=2[S:15][CH2:16][CH2:17][CH3:18])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59516070HCID 59516070, compound

Product 1

HCID 25006309HCID 25006309, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-[4-[4-(cyclohexylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]phenyl]acetate (Intermediate#33) (210 mg, 0.51 mmol) was dissolved in methanol (10 mL) and treated at ambient temperature with a 2M solution of sodium hydroxide (1.27 mL, 2.53 mmol). The mixture was stiffed overnight and then methanol was removed by evaporation under reduced pressure. The clear aqueous solution was diluted with water (20 mL) and acidified to pH3 with 2M HCl. The resulting white precipitate was extracted into ethyl acetate (2×20 mL). The combined extracts were washed with brine (10 mL), dried (MgSO4) and evaporated to give the crude product. The crude product was purified by preparative HPLC using decreasingly polar mixtures of water (containing 0.1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford 2-[4-[4-(cyclohexylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]phenyl]acetic acid. (84 mg, 41%).

Workup

  1. custommethanol was removed by evaporation under reduced pressure
  2. additionThe clear aqueous solution was diluted with water (20 mL)
  3. extractionThe resulting white precipitate was extracted into ethyl acetate (2×20 mL)
  4. washThe combined extracts were washed with brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give the crude product
  8. customThe crude product was purified by preparative HPLC
  9. additionFractions containing the desired compound
  10. customwere evaporated to dryness

Sources & evidence

ORD record
ord-a31a80e2011f418b8a1af8c3e917fd71
Source dataset
uspto-grants-2010_10
Patent number
US07816391B2

Reaction notes

Loading…