Water → HCID 57942712, compound

HRID 1515533Notes

Reaction equation

HRID 1515533 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 58D (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 58E with >90% purity. 1H NMR of the crude 58E 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-e9a73dafbbe14bbc9b91308b24b2fbea
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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