HCID 68797947, compound → HCID 68797312, compound

HRID 268645Notes

Reaction equation

HRID 268645 reaction equation
[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH:5]([OH:38])[CH2:6][CH:7]([OH:37])[CH:8]=[CH: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]>CO.[Pd]>[CH3:1][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:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=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]([CH3:16])[CH3:17]

Participants

4

Reactant 1

HCID 68797947HCID 68797947, compound

Product 1

HCID 68797312HCID 68797312, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 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-hept-6-enoic acid methyl ester (1.190 g, 2.21 mmol) in MeOH (50 ml) was added Pd—C (0.1 g). The reaction vessel was evacuated, flushed with nitrogen and then filled with hydrogen (via balloon). Reaction was stirred at 25° C. for 4 hrs. Reaction was then flushed with nitrogen and filtered through a pad of celite. The filtrate was concentrated and purified by column chromatography (30-40% EtOAc/Hex) to afford 7-{2-(4-fluoro-phenyl)-4-isopropyl-5-[methyl-(2-methyl-benzyl)-carbamoyl]-2H-pyrazol-3-yl}-3,5-dihydroxy-heptanoic acid methyl ester (0.792 g, 66%): MS(APCI+) 540.2 m/z (M+H).

Workup

  1. customThe reaction vessel was evacuated
  2. customflushed with nitrogen
  3. additionfilled with hydrogen (via balloon)
  4. customReaction
  5. customReaction
  6. customwas then flushed with nitrogen
  7. filtrationfiltered through a pad of celite
  8. concentrationThe filtrate was concentrated
  9. custompurified by column chromatography (30-40% EtOAc/Hex)

Sources & evidence

ORD record
ord-65587addf7c7480c8d53f0e2050e741c
Source dataset
uspto-grants-2008_11
Patent number
US07446121B2

Reaction notes

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