Water → HCID 54165423, compound

HRID 486734Notes

Reaction equation

HRID 486734 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:10][S:9][C@@H:8]([CH2:11][SH:12])[CH2:7]1)=[O:5])C.[OH-].[Li+].O>C1COCC1>[C:4]([C@@H:6]1[CH2:10][S:9][C@@H:8]([CH2:11][SH:12])[CH2:7]1)([OH:5])=[O:3]

Participants

5

Procedure

To a stirred solution of trans-4-ethoxycarbonyl-2-mercaptomethyltetrahydrothiophene (compound No. 15-1, 420 mg) in THF (28 ml), 1N lithium hydroxide solution (4.1 ml) was added and the mixture was stirred for 1.5 hours at room temperature. Water was added to the mixture and washed with ethyl acetate. The aqueous layer was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 254 mg (70%) of the titled compound (compound No. 7-1). The physical data was identified with the product obtained in Example 7.

Workup

  1. washwashed with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe oily residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-8a6ccfd9360a49d2a382fc4dc43966e2
Source dataset
uspto-grants-1994_03
Patent number
US05292767

Reaction notes

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