Water → HCID 24961982, compound

HRID 1715837Notes

Reaction equation

HRID 1715837 reaction equation
C([O:3][C:4](=[O:34])[CH2:5][C:6]1[N:7]=[C:8]([NH:11][C:12]([C:14]2[CH:22]=[C:21]3[C:17]([CH2:18][CH2:19][N:20]3[S:23]([C:26]3[CH:31]=[C:30]([CH3:32])[CH:29]=[C:28]([CH3:33])[CH:27]=3)(=[O:25])=[O:24])=[CH:16][CH:15]=2)=[O:13])[S:9][CH:10]=1)C.[OH-].[K+].O>C(O)C>[CH3:32][C:30]1[CH:31]=[C:26]([S:23]([N:20]2[C:21]3[C:17](=[CH:16][CH:15]=[C:14]([C:12]([NH:11][C:8]4[S:9][CH:10]=[C:6]([CH2:5][C:4]([OH:34])=[O:3])[N:7]=4)=[O:13])[CH:22]=3)[CH2:18][CH2:19]2)(=[O:25])=[O:24])[CH:27]=[C:28]([CH3:33])[CH:29]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 86621008HCID 86621008, compound

Product 1

HCID 24961982HCID 24961982, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

(2-{[1-(3,5-Dimethyl-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-thiazol-4-yl)-acetic acid ethyl ester (0.10 g, 0.20 mmol) was suspended in ethanol (1.00 mL) and treated at room temperature with 3N KOH in water (0.20 mL, 0.60 mmol). The mixture was warmed to 50° C. and stirred for 18 hours, then cooled to room temperature and evaporated. The residue was dissolved in water (1.00 mL) and set to pH 1 with HCl 1N. The resulting suspension was filtered, washing with water and the filtrate dried under vacuum to yield (2-{[1-(3,5-dimethyl-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-thiazol-4-yl)-acetic acid as a white solid, 0.09 g (99%), MS (ISP): m/e=470.2 (M−H).

Workup

  1. temperaturecooled to room temperature
  2. customevaporated
  3. dissolutionThe residue was dissolved in water (1.00 mL)
  4. filtrationThe resulting suspension was filtered
  5. washwashing with water
  6. customthe filtrate dried under vacuum

Sources & evidence

ORD record
ord-352ed9bd34584374b56e53ae3ca2b235
Source dataset
uspto-grants-2010_09
Patent number
US07799933B2

Reaction notes

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