HCID 15480015, compound → HCID 18688662, compound

HRID 1873235Notes

Reaction equation

HRID 1873235 reaction equation
[CH3:1][O:2][C:3]([CH2:5][C:6]1[CH:7]=[C:8]([CH:23]([CH3:28])[C:24]([O:26][CH3:27])=[O:25])[CH:9]=[CH:10][C:11]=1[S:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([O:21]C)=O)=[O:4].CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([CH:5]1[C:19](=[O:21])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[S:12][C:11]2[CH:10]=[CH:9][C:8]([CH:23]([CH3:28])[C:24]([O:26][CH3:27])=[O:25])=[CH:7][C:6]1=2)=[O:4]

Participants

4

Reactant 2

HCID 15480015HCID 15480015, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18688662HCID 18688662, compoundYield 110.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl 2-[3-methoxycarbonylmethyl-4-(2-methoxycarbonylphenylthio)phenyl]propionate (prepared in Example 21, 78 mg, 0.19 mmol.), toluene (1 mL) and potassium t-butoxide (43 mg, 0.38 mmol.) were mixed, and the mixture was stirred for 16 hours at room temperature. The reaction mixture was then extracted with ethyl acetate after addition of 2N hydrochloric acid. The ethyl acetate portion was washed with an aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The dried ethyl acetate portion was placed under reduced pressure to distill the solvent off, to leave 78 mg of a pale yellow oil. The oil was subjected to moderate pressure silica gel column chromatography and eluted with ethyl acetate/hexane (1/4, v/v), to give 21 mg of the desired compound as a colorless oil (a mixture of 1:1 diastereomers). The following NMR data are those of the 1:1 diastereomers.

Workup

  1. extractionThe reaction mixture was then extracted with ethyl acetate
  2. additionafter addition of 2N hydrochloric acid
  3. washThe ethyl acetate portion was washed with an aqueous saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationto distill the solvent off,

Sources & evidence

ORD record
ord-2f32fb31e41d4dcdb219559fc08594fc
Source dataset
uspto-grants-2000_08
Patent number
US06111115

Reaction notes

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