Acetic Acid → HCID 86749423, compound

HRID 2293855Notes

Reaction equation

HRID 2293855 reaction equation
CC([Si]([CH:18]([CH2:23][CH2:24][P:25]([CH:29]=[CH:30][C:31]1[C:32]([C:44]2[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=2)=[N:33][C:34]2[C:39]([C:40]=1[CH:41]([CH3:43])[CH3:42])=[CH:38][CH:37]=[CH:36][CH:35]=2)([O:27][CH3:28])=[O:26])[C:19]([O:21][CH3:22])=[O:20])(C1C=CC=CC=1)C1C=CC=CC=1)(C)C.CC(O)=[O:53].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(O)=O.[Na+]>C1COCC1>[F:50][C:47]1[CH:46]=[CH:45][C:44]([C:32]2[C:31](/[CH:30]=[CH:29]/[P:25]([O:27][CH3:28])([CH2:24][C@@H:23]([OH:53])[CH2:18][C:19]([O:21][CH3:22])=[O:20])=[O:26])=[C:40]([CH:41]([CH3:42])[CH3:43])[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:33]=2)=[CH:49][CH:48]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 86749424HCID 86749424, compound

Product 1

HCID 86749423HCID 86749423, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S,E)-3-[[(1,1-Dimethylethyl)diphenylsilyl]-4-[[2-[2-(4-fluorophenyl)-4-(1-methylethyl)-3-quinolinyl]ethenyl]methoxyphosphinyl]butanoic acid, methyl ester(542 mg, 0.749 mmol) in THF (10 ml) was treated with HOAc (215 ul, 226 mg, 3.76 mmol) and tetra-n-butylammonium fluoride (1.0M in THF, 2.25 ml, 2.25 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 (Na2SO4), filtered and stripped to give an oil which was subsequently chromatographed (flash, Merck, SiO2, 1:1 acetone: hexane followed by 20% hexane in acetone). (S,E)-4-[[2-[2-(4-Fluorophenyl)-4-(1-methylethyl)-3-quinolinyl]-ethenyl]methoxyphosphinyl]-3-hydroxybutanoic acid, methyl ester (265 mg, 73%) was obtained as a white foam.

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 followed by 20% hexane in acetone)

Sources & evidence

ORD record
ord-6524933fb7da4ce0b2920e314ffc7ff0
Source dataset
uspto-grants-1997_11
Patent number
US05686433

Reaction notes

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