Water → HCID 57942712, compound

HRID 1438188Notes

Reaction equation

HRID 1438188 reaction equation
[CH:1]1([S:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH:11]2[CH:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14][CH2:13][N:12]2[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:3][CH2:2]1.[OH:28]OS([O-])=O.[K+].[OH2:34]>CCO>[CH:1]1([S:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH:11]2[CH:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14][CH2:13][N:12]2[C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])(=[O:28])=[O:34])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 57942729HCID 57942729, compound

Product 1

HCID 57942712HCID 57942712, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 160D (3.3 g, 8.43 mmol) in EtOH (25 mL) at 0° C. was added a solution of Oxone (11.4 g, 18.6 mmol) in water (60 mL). The mixture was stirred at rt over night. The precipitate was filtered. The filtrate was neutralized with sat. NaHCO3 and EtOH was removed under reduced pressure. The residue was extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated to give crude 160E with >90% purity. 1H NMR of the crude 160E indicated a mixture of cis and trans isomer in ca 1:1 ratio and complicated by the presence of rotomers. LC-MS 424 (M+H).

Workup

  1. filtrationThe precipitate was filtered
  2. customwas removed under reduced pressure
  3. extractionThe residue was extracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-12c2bcd3f6b24889ac903d9adae1f993
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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