Trifluoroacetic acid → HCID 68806562, compound

HRID 268647Notes

Reaction equation

HRID 268647 reaction equation
[Na+].[F:2][C:3]1[CH:4]=[C:5]([CH:37]=[CH:38][CH:39]=1)[CH2:6][N:7]([CH3:36])[C:8]([C:10]1[C:11]([CH:33]([CH3:35])[CH3:34])=[C:12]([CH2:22][CH2:23][CH:24]([OH:32])[CH2:25][CH:26]([OH:31])[CH2:27][C:28]([O-:30])=O)[N:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[N:14]=1)=[O:9].C(O)(C(F)(F)F)=O>CC#N.CCOC(C)=O>[F:2][C:3]1[CH:4]=[C:5]([CH:37]=[CH:38][CH:39]=1)[CH2:6][N:7]([CH3:36])[C:8]([C:10]1[C:11]([CH:33]([CH3:35])[CH3:34])=[C:12]([CH2:22][CH2:23][CH:24]2[CH2:25][CH:26]([OH:31])[CH2:27][C:28](=[O:30])[O:32]2)[N:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[N:14]=1)=[O:9]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 688005877-[5-[(3-Fluoro-benzyl)-methyl-carbamoyl]-2-(4-fluoro-phenyl)-4-isopropyl-2h-pyrazol-3-yl]-3,5-dihydroxy-heptanoic acid sodium salt

Product 1

HCID 68806562HCID 68806562, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a 7-[5-[(3-fluoro-benzyl)-methyl-carbamoyl]-2-(4-fluoro-phenyl)-4-isopropyl-2H-pyrazol-3-yl]-3,5-dihydroxy-heptanoic acid sodium salt (270 mg, 0.49 mmol) in MeCN (50 ml) was slowly added TFA (1.0 mL, 1.23 mmol). The reaction mixture was stirred at 25° C. and monitored by HPLC. After 2 hrs, the reaction was completed. The reaction mixture was diluted with EtOAc (150 ml) and washed with H2O, saturated NaHCO3, and brine. The organic layer was dried over Na2SO4 and concentrated. The crude product was purified by silica gel column chromatography (70% EtOAc/Hex) to afford 1-(4-fluoro-phenyl)-5-[2-(4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-4-isopropyl-1H-pyrazole-3-carboxylic acid (3-fluoro-benzyl)-methyl-amide (210 mg, 84%): MS(APCI+) 512.2 m/z (M+H); H-NMR (CDCl3) [Mixture of rotamers at 25° C.] δ 7.40-7.21, 7.18-6.88, 4.72, 4.611, 4.58-4.48, 4.33-4.24, 2.98-2.93, 2.80-2.68, 2.63, 2.63 2.62, 2.61, 2.57, 2.56, 2.55, 2.17-2.14, 1.80-1.63, 1.61-1.58, 1.31-1.29.

Workup

  1. washwashed with H2O, saturated NaHCO3, and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel column chromatography (70% EtOAc/Hex)

Sources & evidence

ORD record
ord-55f41e529fd0462ea38546f6d2742542
Source dataset
uspto-grants-2008_11
Patent number
US07446121B2

Reaction notes

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