Water → HCID 59479407, compound

HRID 1515537Notes

Reaction equation

HRID 1515537 reaction equation
[CH:1]([S:4][C:5]1[C:6]([C@H:11]2[C@H: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])=[N:7][CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].[OH:28]OS([O-])=O.[K+].[OH2:34]>CCO.CCOC(C)=O>[CH:1]([S:4]([C:5]1[C:6]([C@H:11]2[C@H: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])([CH3:25])[CH3:26])=[O:22])=[N:7][CH:8]=[CH:9][CH:10]=1)(=[O:28])=[O:34])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 59479516HCID 59479516, compound

Product 1

HCID 59479407HCID 59479407, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 65D (1.51 g, 3.83 mmol) in EtOH (25 mL) at 0° C. was added Oxone® (3.53 g, 1.5 eq.) in water (25 mL). The mixture was stirred from 0° C. to rt over 18 h. It was quenched with sat. NaHCO3 and Na2S2O3. The precipitate was removed by filtration and the filtrate was condensed, diluted with EtOAc and washed with brine. The organic layer was dried over Na2SO4. After removal of solvent, the crude was purified by silica column chromatography using gradient EtOAc in hexanes to give 65F (1.51 g, 90% yield). 1H NMR (400 MHz, 90° C., DMSO-d6) δ ppm 1.19 and 1.32 (br s, 18H) 2.10 (br s 1H) 2.34 (br s, 1H) 2.95 (br s, 1H) 3.49 and 3.70 (br 3H), 4.12 (br s, 2H), 5.79 (br s, 1H), 7.57 (br s, 1H), 8.20 (br s, 1H), 8.81 (br s, 1 H). LS-MS 427 (M+H).

Workup

  1. customIt was quenched with sat. NaHCO3 and Na2S2O3
  2. customThe precipitate was removed by filtration
  3. customcondensed
  4. washwashed with brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customAfter removal of solvent
  7. customthe crude was purified by silica column chromatography

Sources & evidence

ORD record
ord-b4fc7d682cab4ac295bfda7594eafea8
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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