Hydrochloric Acid → HCID 86611028, compound

HRID 2245917Notes

Reaction equation

HRID 2245917 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]([OH:13])[C@H:10]2[OH:11])[OH:9])=[CH:4][C:3]=1[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2([C:33]([O:35]C)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:23][CH:22]=1.Cl>[OH-].[K+].CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]([OH:13])[C@H:10]2[OH:11])[OH:9])=[CH:4][C:3]=1[CH2:20][C:21]1[CH:22]=[CH:23][C:24]([O:27][C:28]2([C:33]([OH:35])=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86611027HCID 86611027, compound

Product 1

HCID 86611028HCID 86611028, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

A solution of 1-chloro-4-(β-D-glucopyranos-1-yl)-2-[4-(1-methoxycarbonyl-cyclopent-1-yloxy)-benzyl]-benzene (0.20 g) in aqueous potassium hydroxide solution (4 mol/l, 5 mL) and methanol (5 mL) is stirred at ambient temperature for 4 h. After neutralizing with aqueous hydrochloric acid (1 mol/l), the mixture is concentrated under reduced pressure, diluted with aqueous NaHCO3 solution and extracted with ethyl acetate. The combined organic phases are dried (Na2SO4), the solvent is removed and the residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0→4:1).

Workup

  1. concentrationthe mixture is concentrated under reduced pressure
  2. additiondiluted with aqueous NaHCO3 solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried (Na2SO4)
  5. customthe solvent is removed
  6. customthe residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0→4:1)

Sources & evidence

ORD record
ord-44100a696ad041a68304f0e21641b32b
Source dataset
uspto-grants-2010_03
Patent number
US07683160B2

Reaction notes

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