Acetic Acid → HCID 86749429, compound

HRID 2295223Notes

Reaction equation

HRID 2295223 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:25][CH3:26])([CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[O:17])=[C:12]([CH:27]([CH3:29])[CH3:28])[CH:11]=[C:10]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:9]=2)=[CH:4][CH:3]=1.CC(O)=O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(O)=O.[Na+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13](/[CH:14]=[CH:15]/[P@@:16]([O:25][CH3:26])([CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[O:17])=[C:12]([CH:27]([CH3:28])[CH3:29])[CH:11]=[C:10]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 86749430HCID 86749430, compound

Product 1

HCID 86749429HCID 86749429, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S,E)-3-[[1,1-Dimethylethyl)-diphenylsilyl]oxy]-4-[[2-[2-(4-fluorophenyl)-4-(1-methylethyl)-6-phenyl-3-pyridinyl]ethenyl]-methoxyphosphinyl]butanoic acid, methyl ester (241 mg, 0.321 mmol) in THF (7 ml) was treated with HOAc (92 ul, 96 mg, 1.61 mmol) and tetra-n-butylammonium fluoride (1.0M in THF, 963 ul, 0.963 mmol). After stirring at room temperature for 18 hours, the solution was poured into saturated NaHCO3 and extracted with EtOAc. The EtOAc extract was washed with brine, dried, (Na2 SO4), filtered, and stripped to give an oil which was subsequently chromatographed (flash, Merck SiO2, 1:1 acetone:hexane followed 100% acetone). (S,E)-4-[[2-[2-(4-Fluorophenyl)-4-(1-methylethyl)-6-phenyl-3-pyridinyl]ethenyl]-methoxyphosphinyl]butanoic acid, methyl ester (124 mg, 76%) was obtained as a colorless oil.

Workup

  1. extractionextracted with EtOAc
  2. extractionThe EtOAc extract
  3. washwas washed with brine
  4. customdried, (Na2 SO4),
  5. filtrationfiltered
  6. customto give an oil which
  7. customwas subsequently chromatographed (flash, Merck SiO2, 1:1 acetone:hexane followed 100% acetone)

Sources & evidence

ORD record
ord-ca73e4ae1f5c43a09b04aaf74f5d22a5
Source dataset
uspto-grants-1997_11
Patent number
US05691322

Reaction notes

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