Water → HCID 25160411, compound

HRID 1047690Notes

Reaction equation

HRID 1047690 reaction equation
C([O:3][C:4]([C:6]1([NH:15][S:16]([C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[C:20]=2[O:27][CH2:28][CH:29]=[CH2:30])(=[O:18])=[O:17])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])C.[OH-].[K+].O>CCO>[CH2:28]([O:27][C:20]1[C:21]([Cl:26])=[CH:22][C:23]([Cl:25])=[CH:24][C:19]=1[S:16]([NH:15][C:6]1([C:4]([OH:5])=[O:3])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)(=[O:18])=[O:17])[CH:29]=[CH2:30]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 59314340HCID 59314340, compound

Product 1

HCID 25160411HCID 25160411, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 2-(2-allyloxy-3,5-dichloro-benzenesulfonylamino)-indan-2-carboxylic acid ethyl ester (33) (143 mg, 0.30 mmol) and KOH (500 mg, 8.9 mmol) is dissolved in EtOH (5 mL) and water (0.5 mL) under a water bath. The water bath is removed when KOH is completely dissolved and the resulting reaction solution is stirred at RT for 8 h. After concentration in vacuo, the residue is dissolved in water (20 mL) and acidified with conc. HCl until pH˜3. After filtration, the solid is purified by HPLC to give a pure product (34) as white solid (91 mg, 69%).

Workup

  1. customThe water bath is removed when KOH
  2. dissolutionis completely dissolved
  3. customthe resulting reaction solution
  4. concentrationAfter concentration in vacuo
  5. dissolutionthe residue is dissolved in water (20 mL)
  6. filtrationAfter filtration
  7. customthe solid is purified by HPLC

Sources & evidence

ORD record
ord-be1286457b8a4968a1334a06a837bc40
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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