Acetic Acid → HCID 59557758, compound

HRID 425051Notes

Reaction equation

HRID 425051 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]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([CH2:33][CH3:34])=[CH:29][CH:28]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:35][O:36][C:37](=[O:39])[CH3:38])(=[O:3])[CH3:2].CC(O)=[O:42]>>[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]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([C:33](=[O:42])[CH3:34])=[CH:31][CH:32]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:35][O:36][C:37](=[O:39])[CH3:38])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 11671302HCID 11671302, compound

Product 1

HCID 59557758HCID 59557758, compound

Procedure

To a stirred solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-ethylbenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (intermediate AX) (10 g, 10.83 mmol) (prepared by methods analogous to those described in US20040138439) in AcOH (130 mL) at 120° C. was added K2CrO7 (6.3 g, 21.42 mmol) in one portion. The mixture was stirred for 22 h at the same temperature. Volatiles were removed under reduced pressure, AcOEt was added, and the solids were removed by filtration. The organic layer was washed with a saturated solution of NaHCO3 and brine prior to drying over Na2SO4. Concentration of the organic solution and purification of the resulting residue by silical gel column (PE:EA=3:1) provided intermediate AY (2.3 g).

Workup

  1. customat 120° C.
  2. customVolatiles were removed under reduced pressure, AcOEt
  3. additionwas added
  4. customthe solids were removed by filtration
  5. washThe organic layer was washed with a saturated solution of NaHCO3 and brine
  6. dry with materialto drying over Na2SO4
  7. customConcentration of the organic solution and purification of the resulting residue by silical gel column (PE:EA=3:1)
  8. customprovided intermediate AY (2.3 g)

Sources & evidence

ORD record
ord-6753c941a782405c81db5bdff4b187ef
Source dataset
uspto-grants-2012_01
Patent number
US08106021B2

Reaction notes

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