Ethanol → HCID 59135783, compound

HRID 2239108Notes

Reaction equation

HRID 2239108 reaction equation
[CH3:1][N:2]([S:23]([C:26]1[S:27][CH:28]=[CH:29][N:30]=1)(=[O:25])=[O:24])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][CH:14]([CH2:17][C:18]([O:20]CC)=[O:19])[CH2:15][N:16]=1)=[CH:8]2.O1CCCC1.C(O)C.[OH-].[Na+]>C(OCC)(=O)C.Cl>[CH3:1][N:2]([S:23]([C:26]1[S:27][CH:28]=[CH:29][N:30]=1)(=[O:24])=[O:25])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][CH:14]([CH2:17][C:18]([OH:20])=[O:19])[CH2:15][N:16]=1)=[CH:8]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-4a6484858d4b44b686ed9928d9bdf09e
Source dataset
uspto-grants-2010_05
Patent number
US07718798B2

Reaction notes

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