Tetrahydrofuran → HCID 57901735, compound

HRID 1851533Notes

Reaction equation

HRID 1851533 reaction equation
[CH3:1][N:2]([S:25]([C:28]1[S:29][CH:30]=[CH:31][CH:32]=1)(=[O:27])=[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][O:18][CH2:19][C:20]([O:22]CC)=[O:21])=[CH:15][N:16]=1)=[CH:8]2.[OH-].[Na+].O1CCCC1>CO>[CH3:1][N:2]([S:25]([C:28]1[S:29][CH:30]=[CH:31][CH:32]=1)(=[O:27])=[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][O:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:15][N:16]=1)=[CH:8]2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57901826HCID 57901826, compound

Product 1

HCID 57901735HCID 57901735, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl [(2-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazol-5-yl)methoxy]acetate (0.08 g), 1N aqueous sodium hydroxide solution (0.30 mL), tetrahydrofuran (4 mL) and methanol (4 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 (0.04 g, yield 45%) as pale-yellow crystals. melting point 197-198° 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-828e2d89c34846d0ac4813bde30b1c11
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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