Sodium Hydroxide → 2-Methoxy-3-(2-carboxyethylthio)-3-[2-(8-phenyloctyl)phenyl]propanoic acid

HRID 620557Notes

Reaction equation

HRID 620557 reaction equation
[CH3:1][O:2][CH:3]([CH:8]([S:29][CH2:30][CH2:31][C:32]([O:34]C)=[O:33])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:4]([O:6]C)=[O:5].[OH-].[Na+]>CO>[CH3:1][O:2][CH:3]([CH:8]([S:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15617507Methyl 2-methoxy-3-(2-carbomethoxyethylthio)-3-[2-(8-phenyloctyl)phenyl]propanoate

Product 1

HCID 156175112-Methoxy-3-(2-carboxyethylthio)-3-[2-(8-phenyloctyl)phenyl]propanoic acidYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 2-methoxy-3-(2-carbomethoxyethylthio)-3-[2-(8-phenyloctyl)phenyl]propanoate (0.5807 g, 1.2 mmoles) in methanol (5 ml) under argon was cooled to 0° C., after which 10% sodium hydroxide (1.5 ml, 3.5 mmoles) was added. The mixture was permitted to warm to room temperature and stirred for 2 hours. The methanol was evaporated and the mixture diluted with water. The pH of the aqueous layer was adjusted to 2 with dilute hydrochloric acid and extracted with ether. The organic phase was dried over magnesium sulfate, filtered and evaporated. The diastereomeric mixture of products was separated on a silica column using 23% ethyl acetate in hexane plus 0.5% formic acid. Five runs were made and the fractions analyzed on an analytical column. The separation provided both diastereomers in greater than 99% purity. The erythro isomer was obtained in 28% yield and the threo isomer in 22%.

Workup

  1. customThe methanol was evaporated
  2. additionthe mixture diluted with water
  3. extractionextracted with ether
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. additionThe diastereomeric mixture of products
  8. customwas separated on a silica column
  9. customThe separation
  10. customprovided both diastereomers in greater than 99% purity
  11. customThe erythro isomer was obtained in 28% yield

Sources & evidence

ORD record
ord-1ba82ea1e81b4379965911354c5ed12d
Source dataset
uspto-grants-1989_04
Patent number
US04820719

Reaction notes

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