Cesium carbonate → HCID 92261445, compound

HRID 705326Notes

Reaction equation

HRID 705326 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[CH:22]=[CH:21][C:14]([O:15][CH2:16][C@H:17]([OH:20])[CH2:18][OH:19])=[CH:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1C=CC(S(O[CH2:40][C@@H:41]2[O:43][CH2:42]2)(=O)=O)=CC=1>C(#N)C>[O:43]1[CH2:42][C@@H:41]1[CH2:40][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:11]2[CH:12]=[CH:13][C:14]([O:15][CH2:16][C@H:17]([OH:20])[CH2:18][OH:19])=[CH:21][CH:22]=2)([CH3:9])[CH3:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 154187Glycidyl tosylate, (R)-HCID 117689785HCID 117689785, compound

Product 1

HCID 92261445HCID 92261445, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a stirred solution of (R)-3-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)propane-1,2-diol (3.77 g, 12.49 mmol, 1.0 equiv) in anhydrous acetonitrile (35 mL) at rt was added cesium carbonate (6.1 g, 18.73 mmol, 1.5 equiv), and the mixture was stirred for 20 min under argon atmosphere. A solution of (2R)-(−)-glycidyl tosylate 98% (4.3 g, 18.73 mmol, 1.5 equiv) in anhydrous acetonitrile (8 mL) was added slowly via syringe, and the mixture was allowed to react at 30° C. for 120 h. The reaction mixture was quenched at room temperature with a saturated solution of ammonium chloride (5 mL). The mixture was extracted with ethyl acetate (3×10 mL). The organic layer was washed with deionized water (10 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel (eluent: 5% to 10% methanol in dichloromethane) to provide the title compound (4.1 g, 91%) as a transparent foam.

Workup

  1. customto react at 30° C. for 120 h
  2. customThe reaction mixture was quenched at room temperature with a saturated solution of ammonium chloride (5 mL)
  3. extractionThe mixture was extracted with ethyl acetate (3×10 mL)
  4. washThe organic layer was washed with deionized water (10 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by flash column chromatography on silica gel (eluent: 5% to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-10b1443f17934c9e8a5b7b3a2b1294f6
Source dataset
uspto-grants-2015_11
Patent number
US09173939B2

Reaction notes

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