Hydrochloric Acid → HCID 11978591, compound

HRID 1851628Notes

Reaction equation

HRID 1851628 reaction equation
[CH2:1]([N:3]([S:30]([C:33]1[S:34][CH:35]=[CH:36][CH:37]=1)(=[O:32])=[O:31])[C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]1[S:14][C:15]([CH2:18][O:19][C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][CH:21]=3)=[CH:16][N:17]=1)=[CH:9]2)[CH3:2].O1CCCC1.[OH-].[Na+].Cl>C(OCC)(=O)C.CO>[CH2:1]([N:3]([S:30]([C:33]1[S:34][CH:35]=[CH:36][CH:37]=1)(=[O:31])=[O:32])[C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]1[S:14][C:15]([CH2:18][O:19][C:20]3[CH:21]=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[CH:28][CH:29]=3)=[CH:16][N:17]=1)=[CH:9]2)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57901656HCID 57901656, compound

Product 1

HCID 11978591HCID 11978591, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-[(2-{7-[ethyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazol-5-yl)methoxy]benzoate (98 mg), tetrahydrofuran (2 mL), methanol (2 mL) and 1N aqueous sodium hydroxide solution (2 mL) was stirred at 50° C. for 16 hr. The reaction mixture was acidified with 1N hydrochloride, diluted with ethyl acetate and washed with saturated brine. The organic layer was dried over magnesium sulfate and filtrated. The filtrate was concentrated, and the residue was subjected to silica gel column chromatography and recrystallized from an ethyl acetate-hexane (4:1) mixture to give the title compound (51 mg, yield 54%) as crystals. melting point 188° C.

Workup

  1. washwashed with saturated brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltrated
  4. concentrationThe filtrate was concentrated
  5. customrecrystallized from an ethyl acetate-hexane (4:1) mixture

Sources & evidence

ORD record
ord-1fee3276b38143a89dfbe2c7b18bc1b9
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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