HCID 68381587, compound → HCID 67118500, compound

HRID 1188972Notes

Reaction equation

HRID 1188972 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([O:29][C:30]2[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:32][CH:31]=2)[CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]1[S:19][CH:20]([CH2:23][C:24]([O:26]CC)=[O:25])[CH2:21][N:22]=1)=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1.C(O)C.[OH-].[Na+]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([O:29][C:30]2[CH:31]=[CH:32][C:33]([S:36]([CH3:39])(=[O:37])=[O:38])=[CH:34][CH:35]=2)[CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]1[S:19][CH:20]([CH2:23][C:24]([OH:26])=[O:25])[CH2:21][N:22]=1)=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 68381587HCID 68381587, compound

Product 1

HCID 67118500HCID 67118500, compoundYield 67.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Ethyl (2-{7-(benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetate (1.0 g) was dissolved in a mixed solvent of tetrahydrofuran (6 mL)-ethanol (6 mL), 1M aqueous sodium hydroxide solution (6 mL) was added, and the mixture was stirred at room temperature for 10 min. The reaction solution was concentrated under reduced pressure. Water was added to the residue, and the mixture was neutralized with 1M hydrochloric acid, and filtered. The obtained solid was washed successively with water, ethanol and diethyl ether to give the title compound (640 mg, yield 67%) as a pale-orange solid. The obtained solid was recrystallized from ethanol-hexane to give colorless crystals. melting point 218-219° C. MS 537 (MH+).

Workup

  1. additionwas added
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionWater was added to the residue
  4. filtrationfiltered
  5. washThe obtained solid was washed successively with water, ethanol and diethyl ether

Sources & evidence

ORD record
ord-f1d0ff3d703c4f4c96c90fab0a0a942a
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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