Sodium Hydroxide → HCID 15617539, compound

HRID 620562Notes

Reaction equation

HRID 620562 reaction equation
[OH:1][CH:2]([CH:7]([S:27][CH2:28][CH2:29][C:30]([O:32]C)=[O:31])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[O:23][CH:24]=[CH:25][CH:26]=1)[C:3]([O:5]C)=[O:4].[OH-].[Na+]>CO>[OH:1][CH:2]([CH:7]([S:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[O:23][CH:24]=[CH:25][CH:26]=1)[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15617538HCID 15617538, compound

Product 1

HCID 15617539HCID 15617539, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 2-hydroxy-3-(2-carbomethoxyethylthio)-3-[2-(8-(2-furyl)octyl)phenyl]propanoate (0.068 g, 0.14 mmoles) was dissolved in methanol (2.0 ml), under argon, cooled to 0° C. and a 1N sodium hydroxide solution (0.54 ml) was added dropwise. The ice bath was removed and the reaction mixture permitted to warm to room temperature. After 5 hours, the methanol was evaporated and the residue diluted with water. The pH of the aqueous layer was adjusted to 2 with dilute hydrochloric acid. The acidic layer was then extracted with ethyl acetate, dried over magnesium sulfate, filtered and evaporated. The residue was flash chromatographed on silica gel to provide the desired product as a mixture of diastereomers, -log KB value 7.7.

Workup

  1. customThe ice bath was removed
  2. temperatureto warm to room temperature
  3. customthe methanol was evaporated
  4. additionthe residue diluted with water
  5. extractionThe acidic layer was then extracted with ethyl acetate
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customchromatographed on silica gel

Sources & evidence

ORD record
ord-c6eca7e881ce4ad3836cf6c47ba681fb
Source dataset
uspto-grants-1989_04
Patent number
US04820719

Reaction notes

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