HCID 86746698, compound → HCID 9806505, compound

HRID 1590082Notes

Reaction equation

HRID 1590082 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH:14]=[CH:15][P:16]([O:26][CH3:27])([CH2:18][C@@H:19]([OH:25])[CH2:20][C:21]([O:23][CH3:24])=[O:22])=[O:17])=[C:12]([CH:28]([CH3:30])[CH3:29])[N:11]=[C:10]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[N:9]=2)=[CH:4][CH:3]=1>[Pd].CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH2:14][CH2:15][P:16]([O:26][CH3:27])([CH2:18][C@@H:19]([OH:25])[CH2:20][C:21]([O:23][CH3:24])=[O:22])=[O:17])=[C:12]([CH:28]([CH3:30])[CH3:29])[N:11]=[C:10]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86746698HCID 86746698, compound

Product 1

HCID 9806505HCID 9806505, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (0.026 gm, 0.024 mmol) was added to a methanol solution (30 ml) of (S)-4-[[2-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-phenyl-5-pyrimidinyl]ethenyl]methoxyphosphinyl]-3-hydroxybutanoic acid, methyl ester obtained in Example 3 above (0.125 gm, 0.24 mmol) which had been purged with argon for 15 minutes. The solution was then placed under 50 psi of hydrogen on a Parr apparatus and shaken for 6 days. The flask was then taken off the Parr apparatus and the solution filtered through a pad of celite which was washed with methanol. The filtrate was concentrated to give a clear oil which was subsequently purified by flash chromatography on Merck silica gel in 30-70% acetone in hexane. Product fractions were combined and concentrated to afford the title compound as a white solid (0.080 gm, 64%). TLC: Rf =0.41 (50% acetone in hexane).

Workup

  1. customhad been purged with argon for 15 minutes
  2. filtrationthe solution filtered through a pad of celite which
  3. washwas washed with methanol
  4. concentrationThe filtrate was concentrated
  5. customto give a clear oil which
  6. customwas subsequently purified by flash chromatography on Merck silica gel in 30-70% acetone in hexane
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-34cc3909fd1c4b5a9111678ea19ab30f
Source dataset
uspto-grants-1993_04
Patent number
US05202327

Reaction notes

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