Hydrochloric Acid → HCID 58081010, compound

HRID 1042166Notes

Reaction equation

HRID 1042166 reaction equation
C([O:3][C:4](=[O:39])[CH2:5][CH:6]1[S:10][C:9]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([O:20][C:21]2[CH:22]=[N:23][C:24]([CH2:27][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:25][CH:26]=2)=[CH:15][C:14]=3[O:32][CH:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)=[N:8][CH2:7]1)C.[OH-].[Na+].Cl>C(O)C.O1CCCC1>[CH3:31][S:28]([CH2:27][C:24]1[N:23]=[CH:22][C:21]([O:20][C:16]2[CH:17]=[C:18]3[C:13](=[C:14]([O:32][CH:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)[CH:15]=2)[NH:12][C:11]([C:9]2[S:10][CH:6]([CH2:5][C:4]([OH:39])=[O:3])[CH2:7][N:8]=2)=[CH:19]3)=[CH:26][CH:25]=1)(=[O:29])=[O:30]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58081048HCID 58081048, compound

Product 1

HCID 58081010HCID 58081010, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl{2-[5-({6-[(methylsulfonyl)methyl]pyridin-3-yl}oxy)-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetate (1.0 g) in ethanol (10 mL) and tetrahydrofuran (10 mL) was added 1N aqueous sodium hydroxide solution (5 mL), and the mixture was stirred at room temperature for 15 hr. To the reaction mixture was added 1N hydrochloric acid (5 mL), and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound (0.95 g, yield 100%) as a yellow amorphous solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4df25a3f001846a7b430e06a61dd15f3
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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