Ethyl Acetate → HCID 68796891, compound

HRID 268644Notes

Reaction equation

HRID 268644 reaction equation
[CH3:1][O:2][C:3](=[O:46])[CH2:4][C:5](=[O:45])[CH2:6][CH:7]([O:37][Si](C(C)(C)C)(C)C)[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].CCOC(C)=O>CC#N.O>[CH3:1][O:2][C:3](=[O:46])[CH2:4][C:5](=[O:45])[CH2:6][CH:7]([OH:37])[CH:8]=[CH: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

5

Reactant 2

HCID 8857Ethyl AcetateHCID 68796982HCID 68796982, compound

Product 1

HCID 68796891HCID 68796891, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 5-(tert-butyl-dimethyl-silanyloxy)-7-{2-(4-fluoro-phenyl)-4-isopropyl-5-[methyl-(2-methyl-benzyl)-carbamoyl]-2H-pyrazol-3-yl}-3-oxo-hept-6-enoic acid methyl ester (2.48 g, 3.82 mmol) in MeCN (40 mL) at 25° C. was added HF (2.5 mL of 48% in water). Reaction was stirred at 25° C. for 16 hrs. Subsequently, EtOAc (100 mL) and water (100 mL) were added and the organic layer was separated, dried and concentrated. Product was purified by column chromatography (30%-50% EtOAc-Hex) to afford 7-{2-(4-fluoro-phenyl)-4-isopropyl-5-[methyl-(2-methyl-benzyl)-carbamoyl]-2H-pyrazol-3-yl}-5-hydroxy-3-oxo-hept-6-enoic acid methyl ester (2.03 g, 98.0%): MS(APCI+) 536.4 m/z (M+H).

Workup

  1. customReaction
  2. customthe organic layer was separated
  3. customdried
  4. concentrationconcentrated
  5. customProduct was purified by column chromatography (30%-50% EtOAc-Hex)

Sources & evidence

ORD record
ord-d7e98a5fc3044edfb4337698e4ca8672
Source dataset
uspto-grants-2008_11
Patent number
US07446121B2

Reaction notes

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