Cesium carbonate → HCID 89442788, compound

HRID 1474612Notes

Reaction equation

HRID 1474612 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([O:19][CH3:20])[O:7][C@H:6]1[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=2)[CH:22]=1)(=[O:3])[CH3:2].Br[CH2:37][CH2:38][O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OC(=O)C)C>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([O:19][CH3:20])[O:7][C@H:6]1[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:37][CH2:38][O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])=[CH:31][CH:30]=2)[CH:22]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 86729312HCID 86729312, compound

Product 1

HCID 89442788HCID 89442788, compoundYield 78.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,3S,4R,5S,6S)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate (300 mg, 0.593 mmol) in dry DMF (6 mL), was added (2-bromoethoxy)(tert-butyl)dimethylsilane (423 mg, 1.78 mmol) and cesium carbonate (578 mg, 1.78 mmol). The reaction mixture was stirred at r.t. for 36 h. After completion of reaction, as confirmed by TLC, the reaction mixture was diluted with ethylacetate (100 mL) and washed with water (3×10 mL). The organic layer was dried over anhydrous Na2SO4 and volatiles were evaporated in vacuo. The residue obtained was purified by column chromatography (silica gel, 2:8 Ethyl acetate:Pet. Ether) to afford title compound (310 mg, 78.8%) as white solid.

Workup

  1. customAfter completion of reaction
  2. washwashed with water (3×10 mL)
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4 and volatiles
  4. customwere evaporated in vacuo
  5. customThe residue obtained
  6. customwas purified by column chromatography (silica gel, 2:8 Ethyl acetate:Pet. Ether)

Sources & evidence

ORD record
ord-a0d813314fec49d884b3b331359c7c86
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

Loading…