Water → HCID 20063871, compound

HRID 359763Notes

Reaction equation

HRID 359763 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][CH:16]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([F:32])[CH:25]=1)[CH:17]([OH:23])[C:18]([O:20]CC)=[O:19].[OH-].[K+].O.S([O-])(O)(=O)=O.[K+]>C(O)C.C(OCC)(=O)C>[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][CH:16]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([F:32])[CH:25]=1)[CH:17]([OH:23])[C:18]([OH:20])=[O:19]

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 516920Potassium bisulfateHCID 20063865HCID 20063865, compound

Product 1

HCID 20063871HCID 20063871, compoundYield 53.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following a procedure similar to that described in Example 1(b), 1.85 g of ethyl 3-(2-amino-5-phenoxyphenyl)thio-3-(3-fluoro-4-methoxyphenyl)-2-hydroxypropionate [prepared as described in step (a) above ] was hydrolyzed in ethanol using an aqueous solution prepared from 334 mg of 85% caustic potash. After water and ethyl acetate had been added to the reaction mixture, its pH was adjusted to a value of 3 by the addition of an aqueous solution of potassium hydrogen sulfate. The mixture was then extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and then concentrated by evaporation under reduced pressure. The residue Was triturated in diethyl ether, filtered and dried to give 922 mg of the title compound.

Workup

  1. extractionThe mixture was then extracted with ethyl acetate
  2. washThe extract was washed with an aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe residue Was triturated in diethyl ether
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-61ee5296b56440db967967a5ac33767e
Source dataset
uspto-grants-1991_03
Patent number
US05002942

Reaction notes

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