Water → (1S)-1,5-Anhydro-1-(3-((5-(4-fluorophenyl)-2-thienyl)methyl)-4-methylphenyl)-D-glucitol hemihydrate

HRID 1893147Notes

Reaction equation

HRID 1893147 reaction equation
[C@@H:1]1([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH2:19][C:20]3[S:21][C:22]([C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)=[CH:23][CH:24]=3)[CH:13]=2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].O>CC(C)=O>[OH2:3].[C@@H:1]1([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH2:19][C:20]3[S:21][C:22]([C:25]4[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=4)=[CH:23][CH:24]=3)[CH:13]=2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].[C@@H:1]1([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH2:19][C:20]3[S:21][C:22]([C:25]4[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=4)=[CH:23][CH:24]=3)[CH:13]=2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3]

Participants

4

Reactant 2

HCID 962WaterHCID 24812758Canagliflozin

Product 1

HCID 24997615(1S)-1,5-Anhydro-1-(3-((5-(4-fluorophenyl)-2-thienyl)methyl)-4-methylphenyl)-D-glucitol hemihydrateYield 137.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

An amorphous powder of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene (1.62 g) was dissolved in acetone (15 ml), and thereto were added H2O (30 ml) and a crystalline seed. The mixture was stirred at room temperature for 18 hours, and the precipitate was collected, washed with acetone—H2O (1:4, 30 ml) and dried under reduced pressure at room temperature to give 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene hemihydrate (1.52 g) as colorless crystals. mp 97-100° C.

Workup

  1. customthe precipitate was collected
  2. washwashed with acetone—H2O (1:4, 30 ml)
  3. customdried under reduced pressure at room temperature

Sources & evidence

ORD record
ord-80eac6eecd6442d2aaa15781589696ff
Source dataset
uspto-grants-2013_08
Patent number
US08513202B2

Reaction notes

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