Water → HCID 69130648, compound

HRID 2253272Notes

Reaction equation

HRID 2253272 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31](=[O:36])[NH:32][C:33]([NH2:35])=[O:34])=[CH:25][CH:24]=3)=[CH:18][CH:17]=2)[C:13]([OH:15])=[O:14])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.C([O-])([O-])=O.[K+].[K+].S(OCC)(O[CH2:47][CH3:48])(=O)=O.O>CS(C)=O>[CH2:47]([O:14][C:13](=[O:15])[C:12]([C:16]1[CH:17]=[CH:18][C:19]([O:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31](=[O:36])[NH:32][C:33]([NH2:35])=[O:34])=[CH:25][CH:24]=2)=[CH:20][CH:21]=1)=[CH:11][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=1)[CH3:48]

Participants

6

Reactant 4

HCID 962WaterHCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 69130617HCID 69130617, compound

Product 1

HCID 69130648HCID 69130648, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 6 (0.40 g, 0.81 mmol) in dry DMSO (3 mL) was added K2CO3 (0.14 g, 0.98 mmol). To this, diethyl sulfate (0.115 g, 0.91 mmol) was added and stirred at room temperature for 30 min. The reaction mixture was poured into water (30 mL) and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and evaporated. The crude product was purified by column chromatography over silica gel and eluted with hexanes-ethyl acetate (3:1). Yield: 0.39 g, 92.2%.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customevaporated
  4. customThe crude product was purified by column chromatography over silica gel
  5. washeluted with hexanes-ethyl acetate (3:1)

Sources & evidence

ORD record
ord-ea3e5b54a7c3430d92c77df80e5996ac
Source dataset
uspto-grants-2008_01
Patent number
US07323496B2

Reaction notes

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