Water → HCID 117830931, compound

HRID 515891Notes

Reaction equation

HRID 515891 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C@H:20]([CH2:21][CH:22]([C:26]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[O:27])C(O)=O)[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl-].[Na+].O>CS(C)=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[C@H:20]([CH2:21][CH2:22][C:26]([N:28]3[CH2:29][CH2:30][O:31][CH2:32][CH2:33]3)=[O:27])[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5234Sodium ChlorideHCID 117831357HCID 117831357, compound

Product 1

HCID 117830931HCID 117830931, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 7.80 g (16.51 mmol) of the compound obtained in Step C in 100 mL of DMSO there are added 1.16 g (19.83 mmol) of solid sodium chloride (NaCl) and then, dropwise, 5 mL of water. The batch is stirred at 130° C. for 1 hour and then the solution is concentrated to 3/4. The reaction mixture is then diluted with dichloromethane and washed successively with saturated aqueous lithium chloride solution and then with brine. The organic phase is then dried over MgSO4, filtered and concentrated to dryness. After purification by chromatography over silica gel using cyclohexane and ethyl acetate as eluants, the expected product is obtained in the form of an oil.

Workup

  1. concentrationthe solution is concentrated to 3/4
  2. additionThe reaction mixture is then diluted with dichloromethane
  3. washwashed successively with saturated aqueous lithium chloride solution
  4. dry with materialThe organic phase is then dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customAfter purification by chromatography over silica gel

Sources & evidence

ORD record
ord-c585954a317548588a4b9d82df534e5e
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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