Hydrochloric Acid → HCID 57616387, compound

HRID 2354302Notes

Reaction equation

HRID 2354302 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([O:20]C)=[O:19])=[CH:14][CH:13]=1)[CH:8]=[C:7]2[C@@H:22]1[O:30][C@H:29]([CH2:31][OH:32])[C@@H:27]([OH:28])[C@H:25]([OH:26])[C@H:23]1[OH:24].[OH-].[Na+].Cl>C(O)C>[C:18]([C:15]1[CH:14]=[CH:13][C:12]([CH2:11][N:9]2[C:10]3[C:6](=[CH:5][CH:4]=[CH:3][C:2]=3[Cl:1])[C:7]([C@@H:22]3[O:30][C@H:29]([CH2:31][OH:32])[C@@H:27]([OH:28])[C@H:25]([OH:26])[C@H:23]3[OH:24])=[CH:8]2)=[CH:17][CH:16]=1)([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57616225HCID 57616225, compound

Product 1

HCID 57616387HCID 57616387, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 7-chloro-3-(β-D-glucopyranosyl)-1-[4-(methoxycarbonyl)benzyl]-1H-indole (71 mg) in ethanol (1 mL) was added 2 mol/L aqueous sodium hydroxide solution (1 mL), and the mixture was stirred at room temperature for 2 hours. To the reaction mixture was added 2 mol/L hydrochloric acid (1 mL), and the solvent was removed under reduced pressure. The residue was purified by solid phase extraction on ODS (washing solvent: water, eluent: methanol) to give the title compound (68 mg).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was purified by solid phase extraction on ODS (washing solvent: water, eluent: methanol)

Sources & evidence

ORD record
ord-3f8b14e10d284dbca360d38bc92beabe
Source dataset
uspto-grants-2010_07
Patent number
US07750145B2

Reaction notes

Loading…