Water → 1-(beta-D-glucopyranosyl)-4-chloro-3-(5-(2-methyl-2H-tetrazol-5-yl)-2-thienylmethyl)benzene

HRID 1625749Notes

Reaction equation

HRID 1625749 reaction equation
[C@@H:1]1([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([CH2:19][C:20]3[S:21][C:22]([C:25]4[NH:29][N:28]=[N:27][N: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].CI.[C:32](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C@@H:1]1([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([CH2:19][C:20]3[S:21][C:22]([C:25]4[N:29]=[N:28][N:27]([CH3:32])[N: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]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178521056HCID 178521056, compound

Product 1

HCID 666081101-(beta-D-glucopyranosyl)-4-chloro-3-(5-(2-methyl-2H-tetrazol-5-yl)-2-thienylmethyl)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(β-D-glucopyranosyl)-4-chloro-3-(5-(1H-tetrazol-5-yl)-2-thienylmethyl)benzene (140 mg) obtained in Example 181 was dissolved in dimethylformamide (5 ml) and added thereto were methyl iodide (100 μl) and potassium carbonate (220 mg). The mixture was stirred at room temperature overnight. The reaction solution was poured into water and the mixture was extracted with ethyl acetate. The extract was washed with brine and dried over sodium sulfate, and the solvent was evaporated under reduced pressure to give the desired 1-(β-D-glucopyranosyl)-4-chloro-3-(5-(2-methyl-2H-tetrazol-5-yl)-2-thienylmethyl)benzene as colorless powder. APCI-Mass m/Z 470/472 (M+NH4).

Workup

  1. additionadded
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6cefcab3200f41dc93807b69e2be984c
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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