Methyl 3-mercaptopropionate → 2-Methoxy-3-(2-carboxyethylthio)-3-[2-(8-phenyloctyl)phenyl]propanoic acid

HRID 2165495Notes

Reaction equation

HRID 2165495 reaction equation
[SH:1][CH2:2][CH2:3][C:4]([O:6]C)=[O:5].[CH3:8][O:9][CH:10]([CH:15](O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:11]([O:13]C)=[O:12]>FC(F)(F)C(O)=O>[CH3:8][O:9][CH:10]([CH:15]([S:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 18050Methyl 3-mercaptopropionateHCID 15617503Methyl 2-methoxy-3-hydroxy-3-[2-(8-phenyloctyl)phenyl]propanoate

Product 1

HCID 156175112-Methoxy-3-(2-carboxyethylthio)-3-[2-(8-phenyloctyl)phenyl]propanoic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To trifluoroacetic acid (100 ml) under argon and cooled to 0° C., was added methyl 3-mercaptopropanoate (0.5 ml, 4.5 mmoles). The mixture was stirred for 10 minutes, after which the ice bath was removed. Methyl 2-methoxy-3-hydroxy-3-[2-(8-phenyloctyl)phenyl]propanoate (1.5 g, 4 mmoles) was added and the mixture stirred for 18 hours. The reaction mixture was evaporated and diluted in methylene chloride. The organic layer was washed with 10% sodium hydroxide (ice cold) followed by ice water. The organic layer was dried over magnesium sulfate, filtered and evaporated. Flash chromatography on silica gel provided the desired product.

Workup

  1. customafter which the ice bath was removed
  2. stirringthe mixture stirred for 18 hours
  3. customThe reaction mixture was evaporated
  4. additiondiluted in methylene chloride
  5. washThe organic layer was washed with 10% sodium hydroxide (ice cold)
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-0995c0c20d974f3b8118f65248c2dafe
Source dataset
uspto-grants-1990_07
Patent number
US04939279

Reaction notes

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