Potassium Hydroxide → HCID 18638892, compound

HRID 847571Notes

Reaction equation

HRID 847571 reaction equation
[CH:1]([S:4][CH2:5][CH2:6][N:7]([C:9]([O:11][C@@H:12]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:13]([O:15]CC1C=CC=CC=1)=[O:14])=[O:10])[CH3:8])([CH3:3])[CH3:2].[OH-].[K+]>C(O)C>[CH:1]([S:4][CH2:5][CH2:6][N:7]([C:9]([O:11][C@@H:12]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:13]([OH:15])=[O:14])=[O:10])[CH3:8])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18638989HCID 18638989, compound

Product 1

HCID 18638892HCID 18638892, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of benzyl 2(S)-[N-(2-isopropylthioethyl)-N-methylaminocarbonyloxy]-3-phenylpropionate (623 mg) in ethanol (10 ml) was added 1 N potassium hydroxide (3 ml) at ambient temperature, and the mixture was stirred at the same temperature for 1 hour. The solution was concentrated in vacuo, and the residue was partitioned between water (20 ml) and diethyl ether (20 ml). The aqueous layer was separated and acidified to pH 2 with 10% hydrochloric acid, and the product was extracted with chloroform (20 ml×2). The extract was washed with water (30 ml) and dried over magnesium sulfate. Evaporation of the solvent gave 2(S)-[N-(2-isopropylthioethyl)-N-methylaminocarbonyloxy]-3-phenylpropionic acid (485 mg).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue was partitioned between water (20 ml) and diethyl ether (20 ml)
  3. customThe aqueous layer was separated
  4. extractionthe product was extracted with chloroform (20 ml×2)
  5. washThe extract was washed with water (30 ml)
  6. dry with materialdried over magnesium sulfate
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-7b3e8a315dac47e0b01b74b651f6e3ef
Source dataset
uspto-grants-1992_08
Patent number
US05142048

Reaction notes

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