Pivaloyl chloride → HCID 58224024, compound

HRID 707213Notes

Reaction equation

HRID 707213 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[C:13](Cl)(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15]>ClCCl.CN(C1C=CN=CC=1)C>[CH3:15][C:14]([CH3:17])([CH3:16])[C:13]([O:1][C@@H:2]1[C@H:3]([O:4][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[C@@H:5]([O:6][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[C@H:7]([O:8][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[C@@H:9]([CH2:11][O:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[O:10]1)=[O:18]

Participants

5

Reactant 2

HCID 62493Pivaloyl chlorideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 58224024HCID 58224024, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

D-glucose (25.0 g, 0.139 mol) was suspended in anhydrous dichloromethane (416 mL) under nitrogen and the resulting mixture was stirred for 5 minutes at room temperature, then cooled to 0° C. and stirred for 10 minutes. To the resulting mixture was then added TEA (154.7 mL), dropwise over about 10-15 min, with stirring; then DMAP (1.25 g, 0.0102 mol) in one portion. To the resulting mixture was added pivaloyl chloride (136 mL) diluted with dichloromethane (83 mL) at 0° C., over 30 min. The ice bath was removed and the resulting mixture stirred at room temperature for 20 hours. The resulting mixture was then poured into dichloromethane (500 mL) and hydrochloric acid (1.5M, 375 mL) and the resulting phases separated. The organic layer was washed with sodium bicarbonate solution (550 g in 500 mL DI water, 1N) and then evaporated to a small volume. To the resulting residue was added ethanol (95%, 240 mL) and the mixture heated to reflux temperature to yield a homogeneous mixture. The resulting mixture was cooled to 0° C., resulting in the formation of white crystals, which were filtered and dried in vacuo at room temperature, overnight, to yield the title compound.

Workup

  1. temperaturecooled to 0° C.
  2. stirringstirred for 10 minutes
  3. stirringwith stirring
  4. customThe ice bath was removed
  5. stirringthe resulting mixture stirred at room temperature for 20 hours
  6. additionThe resulting mixture was then poured into dichloromethane (500 mL) and hydrochloric acid (1.5M, 375 mL)
  7. customthe resulting phases separated
  8. washThe organic layer was washed with sodium bicarbonate solution (550 g in 500 mL DI water, 1N)
  9. customevaporated to a small volume
  10. additionTo the resulting residue was added ethanol (95%, 240 mL)
  11. temperaturethe mixture heated
  12. temperatureto reflux temperature
  13. customto yield a homogeneous mixture
  14. temperatureThe resulting mixture was cooled to 0° C.
  15. customresulting in the formation of white crystals, which
  16. filtrationwere filtered
  17. customdried in vacuo at room temperature, overnight

Sources & evidence

ORD record
ord-874ce815cf1646998c34f66d479b622c
Source dataset
uspto-grants-2015_11
Patent number
US09174971B2

Reaction notes

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