Sodium Hydroxide → HCID 24755191, compound

HRID 268646Notes

Reaction equation

HRID 268646 reaction equation
C[O:2][C:3](=[O:39])[CH2:4][CH:5]([OH:38])[CH2:6][CH:7]([OH:37])[CH2:8][CH2:9][C:10]1[N:11]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[N:12]=[C:13]([C:18](=[O:29])[N:19]([CH3:28])[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[C:14]=1[CH:15]([CH3:17])[CH3:16].[OH-].[Na+:41]>CO>[Na+:41].[F:36][C:33]1[CH:32]=[CH:31][C:30]([N:11]2[C:10]([CH2:9][CH2:8][C@@H:7]([OH:37])[CH2:6][C@@H:5]([OH:38])[CH2:4][C:3]([O-:39])=[O:2])=[C:14]([CH:15]([CH3:17])[CH3:16])[C:13]([C:18](=[O:29])[N:19]([CH3:28])[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH3:27])=[N:12]2)=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68797312HCID 68797312, compound

Product 1

HCID 24755191HCID 24755191, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 7-{2-(4-fluoro-phenyl)-4-isopropyl-5-[methyl-(2-methyl-benzyl)-carbamoyl]-2H-pyrazol-3-yl}-3,5-dihydroxy-heptanoic acid methyl ester (0.7920 g, 1.47 mmol) in MeOH (5 ml), NaOH solution (1.028N, 1.50 ml, 1.54 mmol) was added. The reaction mixture was stirred at 25° C. for 12 hrs. After solvent was evaporated, the crude product was dried azeotopically with toluene (×3). It was dissolved in MeOH/CH2Cl2 mixture (1:9, 10 ml) and diluted with CH2CI2 (15 ml). It was filtered through cotton and the filtrate was concentrated, trituated with Et2O for 12 hrs. The product was isolated by filtration and dried under vacuum at 60° C. for 12 hrs to afford (3R,5R)-7-{2-(4-fluoro-phenyl)-4-isopropyl-5-[methyl-(2-methyl-benzyl)-carbamoyl]-2H-pyrazol-3-yl}-3,5-dihydroxy-heptanoic acid sodium salt (798 mg, 99%): MS(APCI+) 526.3 m/z (M+H); H-NMR (DMSO-d6) [Mixture of rotamers at 25° C.] δ 7.79-7.65, 7.58-7.46, 7.41-7.24, 7.22-7.07, 4.85-4.60, 3.62-3.58, 3.46-3.44, 2.89-2.85, 2.84, 2.74-2.66, 2.54-2.45, 2.29, 1.93-1.88,1.73-1.67, 1.53-1.10.

Workup

  1. customAfter solvent was evaporated
  2. dry with materialthe crude product was dried azeotopically with toluene (×3)
  3. dissolutionIt was dissolved in MeOH/CH2Cl2 mixture (1:9, 10 ml)
  4. additiondiluted with CH2CI2 (15 ml)
  5. filtrationIt was filtered through cotton
  6. concentrationthe filtrate was concentrated
  7. waittrituated with Et2O for 12 hrs
  8. customThe product was isolated by filtration
  9. customdried under vacuum at 60° C. for 12 hrs

Sources & evidence

ORD record
ord-6aca21acf8564bedaedd574a0256d5b5
Source dataset
uspto-grants-2008_11
Patent number
US07446121B2

Reaction notes

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