Dimethyl Sulfate → HCID 86701385, compound

HRID 870837Notes

Reaction equation

HRID 870837 reaction equation
[C:1]([O-])([O-])=O.[K+].[K+].[CH2:7]([O:14][N:15]1[C:21](=[O:22])[N:20]2[CH2:23][C@H:16]1[CH2:17][CH2:18][C@H:19]2[C:24]1[O:25][C:26]([CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[N:27][N:28]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.COS(OC)(=O)=O>CC(C)=O>[CH2:7]([O:14][N:15]1[C:21](=[O:22])[N:20]2[CH2:23][C@H:16]1[CH2:17][CH2:18][C@H:19]2[C:24]1[O:25][C:26]([CH:29]2[CH2:34][CH2:33][N:32]([CH3:1])[CH2:31][CH2:30]2)=[N:27][N:28]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 86700689HCID 86700689, compound

Product 1

HCID 86701385HCID 86701385, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

K2CO3 (621 mg, 4.5 mmol) was added to a solution of crude (2S,5R)-6-(benzyloxy)-2-(5-(piperidin-4-yl)-1,3,4-oxadiazol-2-yl)-1,6-diaza-bicyclo[3.2.1]octan-7-one (988 mg) in acetone (30 mL). Me2SO4 (105 μl, 1.6 mmol) was slowly added at 0° C. The mixture was stirred at rt for 6 h, then concentrated and purified by reverse phase column chromatography (gradient elution 0-80% of acetonitrile in water) to give (2S,5R)-6-(benzyloxy)-2-(5-(1-methylpiperidin-4-yl)-1,3,4-oxadiazol-2-yl)-1,6-diaza-bicyclo[3.2.1]octan-7-one (198 mg, 33% for two steps) as a yellow solid. ESI-MS (EI+, m/z): 398.3 [M+H]+.

Workup

  1. concentrationconcentrated
  2. custompurified by reverse phase column chromatography (gradient elution 0-80% of acetonitrile in water)

Sources & evidence

ORD record
ord-81fd79c1fef34a11b5b75b974fa18b53
Source dataset
uspto-grants-2015_03
Patent number
US08969570B2

Reaction notes

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