Hydrochloric Acid → HCID 59136091, compound

HRID 1960479Notes

Reaction equation

HRID 1960479 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][CH:6]1[S:10][C:9]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[NH:20][S:21]([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)(=[O:23])=[O:22])=[N:8][CH2:7]1)C.[OH-].[K+].Cl>O1CCCC1.CO>[S:25]1[CH:26]=[CH:27][CH:28]=[C:24]1[S:21]([NH:20][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[NH:12][C:11]([C:9]1[S:10][CH:6]([CH2:5][C:4]([OH:29])=[O:3])[CH2:7][N:8]=1)=[CH:19]2)(=[O:23])=[O:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 59135737HCID 59135737, compound

Product 1

HCID 59136091HCID 59136091, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl(2-{7-[(2-thienylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetate (0.49 g) was dissolved in a mixed solvent of tetrahydrofuran (8 mL)-methanol (8 mL). Aqueous potassium hydroxide solution (prepared by dissolving potassium hydroxide (0.25 g) in water (4 mL)) was added to this solution, and the mixture was stirred at room temperature for 15 hr. The reaction solution was acidified with diluted hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced, pressure. The obtained amorphous solid was crystallized from ethyl acetate-hexane to give the title compound (256 mg, yield: 56%) as pale-yellow crystals. MS:422(MH+). melting point >240° C. (decomposition).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced, pressure
  5. customThe obtained amorphous solid was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-be3fae0beabe4991b3efde8eded35d9d
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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