Acetic Acid → HCID 86749419, compound

HRID 2295209Notes

Reaction equation

HRID 2295209 reaction equation
CC([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][C@H:7]([CH2:13][P:14](/[CH:18]=[CH:19]/[C:20]1[C:21]([CH:39]([CH3:41])[CH3:40])=[N:22][C:23]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:24][C:25]=1[C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1)([O:16][CH3:17])=[O:15])[CH2:8][C:9]([O:11][CH3:12])=[O:10])(C)C.CC(O)=O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(O)=O.[Na+]>C1COCC1>[F:32][C:29]1[CH:30]=[CH:31][C:26]([C:25]2[CH:24]=[C:23]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:22]=[C:21]([CH:39]([CH3:40])[CH3:41])[C:20]=2/[CH:19]=[CH:18]/[P:14]([O:16][CH3:17])([CH2:13][C@@H:7]([OH:6])[CH2:8][C:9]([O:11][CH3:12])=[O:10])=[O:15])=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 86749420HCID 86749420, compound

Product 1

HCID 86749419HCID 86749419, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S,E)-3-[[(1,1-Dimethylethyl)-diphenylsilyl]oxy]-4-[[2-[4-(4-fluorophenyl)-2-(1-methylethyl)-6-phenyl-3-pyridinyl]ethenyl]methoxyphosphinyl]butanoic acid, methyl ester (826 mg, 1.10 mmol) in THF (10 ml) was treated with HOAc (320 ul, 336 mg, 5.6 mmol) and tetra-n-butylammonium fluoride (1.0M in THF, 3.3 ml, 3.3 mmol). After stirring at room temperature for 22 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, 30% acetone in hexane followed by 50% acetone in hexane). (S,E)-4-[[2-[4-(4-Fluorophenyl)-2-(1-methylethyl)-6-phenyl-3-pyridinyl]ethenyl]methoxyphosphinyl]-3-hydroxybutanoic acid, methyl ester (497 mg, 88%) was obtained as a white oily foam.

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, 30% acetone in hexane followed by 50% acetone in hexane)

Sources & evidence

ORD record
ord-89336a2a281547548644f3f6876be322
Source dataset
uspto-grants-1997_11
Patent number
US05691322

Reaction notes

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