HCID 86652855, compound → HCID 67118530, compound

HRID 1188979Notes

Reaction equation

HRID 1188979 reaction equation
[C:1]([Si:5]([C:48]([CH3:51])([CH3:50])[CH3:49])([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[O:6][CH2:7][CH:8]([CH3:41])[O:9][C:10]1[CH:11]=[C:12]([O:30][C:31]2[CH:36]=[CH:35][C:34]([S:37]([CH3:40])(=[O:39])=[O:38])=[CH:33][CH:32]=2)[CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]1[S:20][CH:21]([CH2:24][C:25]([O:27]CC)=[O:26])[CH2:22][N:23]=1)=[CH:15]2)([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.C(O)C.[OH-].[Na+]>[C:48]([Si:5]([C:1]([CH3:2])([CH3:4])[CH3:3])([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[O:6][CH2:7][CH:8]([CH3:41])[O:9][C:10]1[CH:11]=[C:12]([O:30][C:31]2[CH:32]=[CH:33][C:34]([S:37]([CH3:40])(=[O:38])=[O:39])=[CH:35][CH:36]=2)[CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]1[S:20][CH:21]([CH2:24][C:25]([OH:27])=[O:26])[CH2:22][N:23]=1)=[CH:15]2)([CH3:51])([CH3:49])[CH3:50]

Participants

5

Reactant 1

HCID 86652855HCID 86652855, compound

Product 1

HCID 67118530HCID 67118530, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Ethyl (2-{7-(2-{[di-tert-butyl(phenyl)silyl]oxy}-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl)acetate (480 mg) was dissolved in a mixed solvent of tetrahydrofuran (10 mL)-ethanol (10 mL), 1M aqueous sodium hydroxide solution (7 mL) was added, and the mixture was stirred at room temperature for 1 hr. The reaction solution was concentrated under reduced pressure. Water was added to the residue, and the mixture was neutralized with 1M hydrochloric acid. The precipitated solid was collected by filtration to give the title compound (320 mg, yield 70%) as a yellow solid. MS 743 (MH+).

Workup

  1. additionwas added
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionWater was added to the residue
  4. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-891d06fbc7694096be6194df36e66842
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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