Hydrochloric Acid → HCID 58236984, compound

HRID 1189018Notes

Reaction equation

HRID 1189018 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([O:25][C:26]2[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:28][N:27]=2)[CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14]1[S:15][CH:16]([CH2:19][C:20]([O:22]CC)=[O:21])[CH2:17][N:18]=1)=[CH:10]2)[CH3:3].O1CCCC1.[OH-].[Na+].Cl>O.C(O)C>[CH3:3][CH:2]([O:4][C:5]1[CH:6]=[C:7]([O:25][C:26]2[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:33])=[O:34])=[CH:28][N:27]=2)[CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14]1[S:15][CH:16]([CH2:19][C:20]([OH:22])=[O:21])[CH2:17][N:18]=1)=[CH:10]2)[CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58237092HCID 58237092, compound

Product 1

HCID 58236984HCID 58236984, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of ethyl {2-[7-(1-methylethoxy)-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetate (980 mg), tetrahydrofuran (10 mL), ethanol (10 mL) and 1M aqueous sodium hydroxide solution (10 mL) was stirred at 50° C. for 3 h. Water and 1M hydrochloric acid (10 mL) were added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residual crystals were washed with ethyl acetate and hexane to give the title compound (830 mg, 89%) as brown crystals. MS 490 (MH+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washThe residual crystals were washed with ethyl acetate and hexane

Sources & evidence

ORD record
ord-1b4460785e744d65b172279681225473
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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