Hydrochloric Acid → 2-[(1,1-Dioxo-1,2-benzoisothiazol-3-yl)thio]-3-(4-benzyloxyphenyl)propionic acid

HRID 1352523Notes

Reaction equation

HRID 1352523 reaction equation
[O:1]=[S:2]1(=[O:32])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([S:11][CH:12]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:20][CH:19]=2)[C:13]([O:15]C)=[O:14])=[N:3]1.[OH-].[K+].Cl.O>CO.O>[O:32]=[S:2]1(=[O:1])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([S:11][CH:12]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[CH:20][CH:19]=2)[C:13]([OH:15])=[O:14])=[N:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 11532849HCID 11532849, compound

Product 1

HCID 117051342-[(1,1-Dioxo-1,2-benzoisothiazol-3-yl)thio]-3-(4-benzyloxyphenyl)propionic acidYield 40%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

The crude product from Step A was dissolved in a MeOH/H2O mixture (2:1, 4 ml). 0.7 g KOH was added to the solution and heated at reflux for 1.5 h. Then the reaction mixture was neutralized with 1M HCl, a small amount of water was added and the mixture extracted with ethyl acetate. The solvent was evaporated. The product was purified by chromatography (SiO2; ethyl acetate). The yield was 40%.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1.5 h
  3. extractionthe mixture extracted with ethyl acetate
  4. customThe solvent was evaporated
  5. customThe product was purified by chromatography (SiO2; ethyl acetate)

Sources & evidence

ORD record
ord-c2cd79fdd7454d9fb40c1d40c13bb6a9
Source dataset
uspto-grants-2007_05
Patent number
US07220766B2

Reaction notes

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