Sodium Hydroxide → HCID 131716920, compound

HRID 1086269Notes

Reaction equation

HRID 1086269 reaction equation
C([O:3][C:4](=[O:23])[C@@H:5]1[CH:9]([C:10](=[O:22])[CH2:11][CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13]2)[S:8][CH2:7][NH:6]1)C.[OH-].[Na+]>C(O)C>[CH2:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:20][CH2:21][CH:12]1[CH2:11][C:10]([CH:9]1[S:8][CH2:7][NH:6][C@@H:5]1[C:4]([OH:23])=[O:3])=[O:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131716919HCID 131716919, compound

Product 1

HCID 131716920HCID 131716920, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2.0 g of 3-(1,2,3,4-tetrahydronaphthalen-2-ylacetyl)-L-thioproline ethyl ester prepared in Reference Example 17 in 23 ml of ethanol was added 37 ml of 1 N sodium hydroxide at room temperature, and the mixture was stirred at the same temperature. After 3 hours, ethanol was evaporated under reduced pressure. After the addition of 100 ml of water and washing with benzene, the water layer was acidified with the addition of diluted hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, the residue was treated with isopropyl ether to produce 1.5 g of colorless crystals of 3-(1,2,3,4-tetrahydronaphthalen-2-ylacetyl)-L-thioproline (yield: 82%).

Workup

  1. customethanol was evaporated under reduced pressure
  2. additionAfter the addition of 100 ml of water
  3. washwashing with benzene
  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 brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customAfter evaporation of the solvent under reduced pressure
  9. additionthe residue was treated with isopropyl ether

Sources & evidence

ORD record
ord-225ea0d5a48e454ba5ebc9d834798273
Source dataset
uspto-grants-1991_07
Patent number
US05028604

Reaction notes

Loading…