Sodium Hydroxide → HCID 24754522, compound

HRID 268641Notes

Reaction equation

HRID 268641 reaction equation
C([O:5][C:6](=[O:40])[CH2:7][CH:8]([OH:39])[CH2:9][CH:10]([OH:38])[CH2:11][CH2:12][C:13]1[N:14]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[N:15]=[C:16]([C:21](=[O:30])[NH:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:17]=1[CH:18]([CH3:20])[CH3:19])(C)(C)C.[OH-].[Na+:42]>CO>[Na+:42].[CH2:23]([NH:22][C:21]([C:16]1[C:17]([CH:18]([CH3:20])[CH3:19])=[C:13]([CH2:12][CH2:11][C@@H:10]([OH:38])[CH2:9][C@@H:8]([OH:39])[CH2:7][C:6]([O-:40])=[O:5])[N:14]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[N:15]=1)=[O:30])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68798188HCID 68798188, compound

Product 1

HCID 24754522HCID 24754522, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 7-[5-benzylcarbamoyl-2-(4-fluoro-phenyl)-4-isopropyl-2H-pyrazol-3-yl]-3,5-dihydroxy-heptanoic acid tert-butyl ester (0.103 g, 0.186 mmol) in MeOH (5 mL) was added 1.0 N NaOH (0.190 mL, 0.195 mmol; commercially available from Sigma Aldrich) and the reaction was stirred at 25° C. for 48 hr after which time the reaction was solvent was removed under reduced pressure. The resulting solid was then azeotroped toluene (3×100 mL) and triturated with diethyl ether to provide a light yellow solid that was dried under vacuum at 60° C. to afford (3R,5R)-7-[5-benzylcarbamoyl-2-(4-fluoro-phenyl)-4-isopropyl-2H-pyrazol-3-yl]-3,5-dihydroxy-heptanoic acid sodium salt (0.091 g, 94%): MS(APCI+): m/z498.2 (M+H); H-NMR (DMSO-d6) δ 8.55 (t, 1 H), 7.53-7.49 (m, 2 H), 7.33-7.13 (m, 7 H), 4.70 (bs, 1 H), 4.34 (d, 2 H), 3.63-3.57 (m, 1 H), 3.45-3.42 (m, 1 H), 2.74-2.66 (m, 1 H), 2.58-2.50 (m, 1 H), 1.95-1.90 (m, 1 H), 1.75-1.69 (m, 1 H), 1.40-1.10 (m, 10 H).

Workup

  1. customwas removed under reduced pressure
  2. customazeotroped toluene (3×100 mL) and triturated with diethyl ether
  3. customto provide a light yellow solid
  4. customthat was dried under vacuum at 60° C.

Sources & evidence

ORD record
ord-94039520581f46fdad5a1f0a01d893a2
Source dataset
uspto-grants-2008_11
Patent number
US07446121B2

Reaction notes

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