Ethanol → HCID 59135783, compound

HRID 1960505Notes

Reaction equation

HRID 1960505 reaction equation
C([O:3][C:4](=[O:30])[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[N:20]([CH3:29])[S:21]([C:24]2[S:25][CH:26]=[CH:27][N:28]=2)(=[O:23])=[O:22])=[N:8][CH2:7]1)C.O1CCCC1.C(O)C.[OH-].[Na+]>C(OCC)(=O)C.Cl>[CH3:29][N:20]([S:21]([C:24]1[S:25][CH:26]=[CH:27][N:28]=1)(=[O:22])=[O:23])[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:30])=[O:3])[CH2:7][N:8]=1)=[CH:19]2

Participants

7

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59136014HCID 59136014, compound

Product 1

HCID 59135783HCID 59135783, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl(2-{7-[methyl(1,3-thiazol-2-ylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetate (300 mg), tetrahydrofuran (5 mL), ethanol (5 mL) and 2N aqueous sodium hydroxide solution (4 mL) was stirred at room temperature for 1 hr. The reaction mixture was diluted with ethyl acetate (100 mL) and 1N hydrochloric acid (50 mL). The organic layer was dried over sodium sulfate, and filtrated, and the filtrate was concentrated. The obtained solid was washed with ethyl acetate to give the title compound (278 mg, yield 98%) as a white solid. melting point 121-123° C.

Workup

  1. dry with materialThe organic layer was dried over sodium sulfate
  2. filtrationfiltrated
  3. concentrationthe filtrate was concentrated
  4. washThe obtained solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-bc410f614c4d46b6a4f430edcd3fb268
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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