Cesium carbonate → HCID 86608942, compound

HRID 2239928Notes

Reaction equation

HRID 2239928 reaction equation
CC1C=CC(S(O[C@H:12]2[CH2:16][CH2:15][O:14][CH2:13]2)(=O)=O)=CC=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C@:24]2([O:33][C@H:32]([CH2:34][OH:35])[C@@H:30]([OH:31])[C@H:28]([OH:29])[C@H:26]2[OH:27])[OH:25])=[CH:20][C:19]=1[CH2:36][C:37]1[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.[Cl-].[Na+].O>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C@:24]2([O:33][C@H:32]([CH2:34][OH:35])[C@@H:30]([OH:31])[C@H:28]([OH:29])[C@H:26]2[OH:27])[OH:25])=[CH:20][C:19]=1[CH2:36][C:37]1[CH:38]=[CH:39][C:40]([O:43][C@@H:12]2[CH2:16][CH2:15][O:14][CH2:13]2)=[CH:41][CH:42]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonate2×HCID 13837326(S)-tetrahydrofuran-3-yl 4-methylbenzenesulfonate2×HCID 866006741-Chloro-4-(beta-glucopyranos-1-yl)-2-(4-hydroxybenzyl)-benzene

Product 1

HCID 86608942HCID 86608942, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
75 °C

Procedure

0.19 g (S)-3-(4-methylphenylsulfonyloxy)-tetrahydrofuran are added to a mixture of 0.20 g 1-chloro-4-(β-D-glucopyranos-1-yl)-2-(4-hydroxybenzyl)-benzene and 0.29 g cesium carbonate in 2.5 ml dimethylformamide. The mixture is stirred at 75° C. for 4 h, before another 0.29 g caesium carbonate and 0.19 g (S)-3-(4-methylphenyl-sulfonyloxy)-tetrahydrofuran are added. After an additional 14 h stirring at 75° C. the mixture is cooled to ambient temperature, and brine is added. The resulting mixture is extracted with ethyl acetate, the combined organic extracts are dried over sodium sulfate, and the solvent is removed. The residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0->5:1).

Workup

  1. additionare added
  2. temperatureis cooled to ambient temperature
  3. extractionThe resulting mixture is extracted with ethyl acetate
  4. dry with materialthe combined organic extracts are dried over sodium sulfate
  5. customthe solvent is removed
  6. customThe residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0->5:1)

Sources & evidence

ORD record
ord-b280df1f66684ad190873a17bf239efa
Source dataset
uspto-grants-2010_05
Patent number
US07723309B2

Reaction notes

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