Acetic Acid → HCID 86749425, compound

HRID 2295218Notes

Reaction equation

HRID 2295218 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:37]([CH3:39])[CH3:38])=[N:22][C:23]2[C:28]([C:29]=1[C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1)=[CH:27][CH:26]=[CH:25][CH:24]=2)([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:36][C:33]1[CH:32]=[CH:31][C:30]([C:29]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=[C:21]([CH:37]([CH3:39])[CH3:38])[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:35][CH:34]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 86749426HCID 86749426, compound

Product 1

HCID 86749425HCID 86749425, compoundYield 93%

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)-3-quinolinyl]ethenyl]methoxyphosphinyl]butanoic acid, methyl ester (1.136 gm, 1.57 mmol) in THF (14 ml) was treated with HOAc (450 ul, 472 mg, 7.9 mmol) and tetra-n-butylammonium fluoride (1.0M in THF, 5.40 ml, 5.40 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 (Na2SO4), filtered, and stripped to give an oil which was subsequently chromatographed (flash, Merck SiO2, 1:1 acetone:hexane). (S,E)-4-[[2-[4-(4-Fluorophenyl)-2-(1-methylethyl)-3-quinolinyl]-ethenyl]methoxyphosphinyl]-3-hydroxybutanoic acid, methyl ester (709 mg, 93%) was obtained as a colorless oil.

Workup

  1. extractionextracted with EtOAc
  2. extractionThe EtOAc extract
  3. washwas washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customto give an oil which
  7. customwas subsequently chromatographed (flash, Merck SiO2, 1:1 acetone:hexane)

Sources & evidence

ORD record
ord-27d75f3c213a4017afb3c4d0fd943897
Source dataset
uspto-grants-1997_11
Patent number
US05691322

Reaction notes

Loading…