Water → HCID 59479418, compound

HRID 1515539Notes

Reaction equation

HRID 1515539 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 59479395HCID 59479395, compound

Product 1

HCID 59479418HCID 59479418, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 65E (0.45 g, 1.15 mmol) in EtOH (8 mL) at 0° C. was added Oxone® (0.99 g, 1.6 mmol, 1.4 eq.) in water (8 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 65J (0.44 g, 81% yield). 1H NMR (400 MHz, 90° C., DMSO-d6) δ ppm 0.88 (t, J=7.15 Hz, 3H) 1.13-1.17 (m, 3H) 1.19-1.27 (m, 9H) 1.34 (d, J=7.15 Hz, 3H) 2.10 (dd, J=7.42, 4.67 Hz, 1H) 2.39 (br s, 1H) 3.45-3.56 (m, 2H) 3.59-3.69 (m, 1H) 3.70-3.80 (m, 3H) 5.86 (d, J=8.25 Hz, 1H) 7.50 (dd, J=7.97, 4.67 Hz, 1H) 8.15 (d, J=7.70 Hz, 1H) 8.76 (d, J=4.40 Hz, 1H), LC-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-4efe69d49d394082addfacac22e6a827
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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