Tetrahydrofuran → HCID 57901696, compound

HRID 1851536Notes

Reaction equation

HRID 1851536 reaction equation
[CH3:1][N:2]([S:24]([C:27]1[S:28][CH:29]=[CH:30][CH:31]=1)(=[O:26])=[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][C:14]([CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])=[CH:15][N:16]=1)=[CH:8]2.[OH-].[Na+].O1CCCC1>CO>[CH3:1][N:2]([S:24]([C:27]1[S:28][CH:29]=[CH:30][CH:31]=1)(=[O:25])=[O:26])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][C:14]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:15][N:16]=1)=[CH:8]2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57901574HCID 57901574, compound

Product 1

HCID 57901696HCID 57901696, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 3-(2-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazol-5-yl)propanate (3.58 g), 2N aqueous sodium hydroxide solution (10.0 mL), tetrahydrofuran (10 mL) and methanol (10 mL) was stirred at 60° C. for 1 hr. The reaction mixture was concentrated, and water was added to the residue. The mixture was acidified with 10% aqueous citric acid solution, and the resulting crystals were filtrated, washed with water, and dried to give the title compound (3.34 g, yield 99%) as pale-yellow crystals. melting point 234-235° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added to the residue
  3. filtrationthe resulting crystals were filtrated
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-53a38c92befa4f61b4e8071642c570ae
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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