Potassium Hydroxide → HCID 10093047, compound

HRID 359768Notes

Reaction equation

HRID 359768 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][C:3]=1[S:15][C@@H:16]([C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=1)[C@@H:17]([OH:31])[C:18]([O:20]C1(C)CCC(C(C)C)CC1)=[O:19].[OH-].[K+]>CO.O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:4][C:3]=1[S:15][C@@H:16]([C:32]1[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=1)[C@@H:17]([OH:31])[C:18]([OH:20])=[O:19]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86744685HCID 86744685, compound

Product 1

HCID 10093047HCID 10093047, compoundYield 65.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4.2 g of l-menthyl (2S, 3S)-3-(2-amino-5-phenoxyphenyl)thio-2-hydroxy-3-(4- methoxyphenyl)propionate [prepared as described in step (a) above] were suspended in 42 ml of methanol, and a solution of 0.89 g of caustic potash dissolved in 5 ml of water was added to the resulting suspension. The resulting mixture was then stirred under reflux for 1 hour. At the end of this time, the methanol was removed by evaporation under reduced pressure, and 60 ml of Water and 60 ml of diethyl ether were added to the residue. The resulting mixture was stirred, and the ethereal layer was then removed. Ethyl acetate was added to the aqueous layer. after which 14.5 ml of 1N aqueous hydrochloric acid were added to neutralize the mixture. The ethyl acetate layer was then separated and dried over anhydrous anhydrous magnesium sulfate. The solvent was removed by evaporation under reduced pressure, and the residual gum Was crystallized using diethyl ether and diisopropyl ether. The crystals obtained were collected by filtration to afford 2.05 g of the title compound. melting at 151-152° C.

Workup

  1. additionwas added to the resulting suspension
  2. temperatureunder reflux for 1 hour
  3. customAt the end of this time, the methanol was removed by evaporation under reduced pressure, and 60 ml of Water and 60 ml of diethyl ether
  4. additionwere added to the residue
  5. stirringThe resulting mixture was stirred
  6. customthe ethereal layer was then removed
  7. additionEthyl acetate was added to the aqueous layer
  8. additionafter which 14.5 ml of 1N aqueous hydrochloric acid were added
  9. customThe ethyl acetate layer was then separated
  10. dry with materialdried over anhydrous anhydrous magnesium sulfate
  11. customThe solvent was removed by evaporation under reduced pressure
  12. customthe residual gum Was crystallized
  13. customThe crystals obtained
  14. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-a85afb86d9fd4efda56f0b5a07215364
Source dataset
uspto-grants-1991_03
Patent number
US05002942

Reaction notes

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