Sodium Hydroxide → 3-(2-indanylacetyl)-L-thioproline

HRID 1086266Notes

Reaction equation

HRID 1086266 reaction equation
C([O:3][C:4](=[O:22])[C@@H:5]1[CH:9]([C:10](=[O:21])[CH2:11][CH:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)[S:8][CH2:7][NH:6]1)C.[OH-].[Na+]>C(O)C>[CH:12]1([CH2:11][C:10]([CH:9]2[S:8][CH2:7][NH:6][C@@H:5]2[C:4]([OH:22])=[O:3])=[O:21])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1317169173-(2-indanylacetyl)-L-thioproline ethyl ester

Product 1

HCID 1317169183-(2-indanylacetyl)-L-thioprolineYield 57.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.45 g of 3-(2-indanylacetyl)-L-thioproline ethyl ester prepared in Reference Example 1 in 17 ml of ethanol was added 28 ml of 1 N sodium hydroxide, and the mixture was stirred at room temperature. After 1 hour, ethanol was evaporated under reduced pressure. Twenty (20) ml of water was added to the residue and the solution was washed with ethyl acetate. The water layer was acidified with the addition of diluted hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, the residue was recrystallized from a mixed solvent of ethyl acetate and n-hexane to produce 0.76 g of 3-(2-indanylacetyl)-L-thioproline (yield: 57%).

Workup

  1. customethanol was evaporated under reduced pressure
  2. additionTwenty (20) ml of water was added to the residue
  3. washthe solution was washed with ethyl acetate
  4. additionThe water layer was acidified with the addition of diluted hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customAfter evaporation of the solvent under reduced pressure
  9. customthe residue was recrystallized from a mixed solvent of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-0bfa0ab2f0bf4b028f90f3762199120e
Source dataset
uspto-grants-1991_07
Patent number
US05028604

Reaction notes

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