HCID 54036334, compound → HCID 129934, compound

HRID 1199173Notes

Reaction equation

HRID 1199173 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)=[C:9]([C:27]2[N:31]([CH3:32])[N:30]=[N:29][N:28]=2)[CH:10]=[CH:11][CH:12]2OC3(CCCCC3)[O:15][CH:14]([CH2:23][C:24]([OH:26])=[O:25])[CH2:13]2)=[CH:4][CH:3]=1>C1COCC1>[F:39][C:36]1[CH:37]=[CH:38][C:33]([C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[C:9]([C:27]2[N:31]([CH3:32])[N:30]=[N:29][N:28]=2)[CH:10]=[CH:11][C@@H:12]2[O:26][C:24](=[O:25])[CH2:23][C@@H:14]([OH:15])[CH2:13]2)=[CH:34][CH:35]=1

Participants

3

Reactant 1

HCID 54036334HCID 54036334, compound

Product 1

HCID 129934HCID 129934, compoundYield 16.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[4,4-bis(4-fluorophenyl)-3-(1-methyl-1H-tetrazol-5-yl)-1,3-butadienyl]-1,5-dioxaspiro[5.5]undecane-2-acetic acid (280 mg, 0.52 mmol) in 20 mL of THF/0.5N HCl (1:1) was allowed to stand at ambient temperature for 26 hours. The solution was partitioned between brine and ethyl acetate. The organic layer was washed with brine (2x), dried (Na2SO4) and concentrated. The resultant foam (126 mg) was dissolved in dry methylene chloride (10 mL) and treated with 1-cyclohexyl-3-(2-morpholinomethyl) carbodiimide metho-p-toluenesulfonate (0.24 g). After 16 hours at ambient temperature, the solution was evaporated under reduced pressure and the residue was purified by silica gel chromatography using ethyl acetate as eluent. The appropriate fractions afforded 38 mg (16.6%) of the title compound as a colorless oil which is a racemic mixture of the compound of Example 7.

Workup

  1. customThe solution was partitioned between brine and ethyl acetate
  2. washThe organic layer was washed with brine (2x)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. dissolutionThe resultant foam (126 mg) was dissolved in dry methylene chloride (10 mL)
  6. additiontreated with 1-cyclohexyl-3-(2-morpholinomethyl) carbodiimide metho-p-toluenesulfonate (0.24 g)
  7. waitAfter 16 hours at ambient temperature
  8. customthe solution was evaporated under reduced pressure
  9. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-41965ac700a84a39b29276fd0a7fc2b3
Source dataset
uspto-grants-1990_02
Patent number
US04898950

Reaction notes

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