Potassium Hydroxide → HCID 15434321, compound

HRID 1107913Notes

Reaction equation

HRID 1107913 reaction equation
[OH-].[K+].[CH2:3]([S:10][CH2:11][CH2:12][CH:13]([N:18]([CH2:30][CH:31]([CH3:33])[CH3:32])[S:19]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)(=[O:21])=[O:20])[C:14]([O:16]C)=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O1CCOCC1.O>[CH2:3]([S:10][CH2:11][CH2:12][CH:13]([N:18]([CH2:30][CH:31]([CH3:33])[CH3:32])[S:19]([C:22]1[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)(=[O:21])=[O:20])[C:14]([OH:16])=[O:15])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 10895907HCID 10895907, compound

Product 1

HCID 15434321HCID 15434321, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

1.77 mmol of potassium hydroxide are added to 0.95 mmol of the compound obtained in Step C in a 3/1 mixture of dioxane/water. After stirring for 3 hours at 50° C., the dioxane is evaporated off, the residual aqueous phase is diluted with water, acidified to pH 2 by the addition of a 5% hydrochloric acid solution, and then extracted with ethyl acetate. The combined organic phases are washed, dried and filtered and then evaporated under reduced pressure. Chromatography on silica gel (dichloromethane/methanol: 93/7) allows the expected product to be isolated in the form of syrup.

Workup

  1. customthe dioxane is evaporated off
  2. additionthe residual aqueous phase is diluted with water
  3. additionacidified to pH 2 by the addition of a 5% hydrochloric acid solution
  4. extractionextracted with ethyl acetate
  5. washThe combined organic phases are washed
  6. customdried
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customto be isolated in the form of syrup

Sources & evidence

ORD record
ord-5c700bcc7be7450e87f18effc79a8ded
Source dataset
uspto-grants-2000_05
Patent number
US06063816

Reaction notes

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