Dichloromethane → HCID 21350203, compound

HRID 1359377Notes

Reaction equation

HRID 1359377 reaction equation
ClCCl.C(N(S(F)(F)[F:10])CC)C.[CH2:13]([C:20]1[C:25]([O:26][CH2:27][O:28][CH3:29])=[CH:24][CH:23]=[C:22]([N:30]2[CH2:34][CH2:33][C@@H:32](O)[C:31]2=[O:36])[N:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O>[CH2:13]([C:20]1[C:25]([O:26][CH2:27][O:28][CH3:29])=[CH:24][CH:23]=[C:22]([N:30]2[CH2:34][CH2:33][C@@H:32]([F:10])[C:31]2=[O:36])[N:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 123472(Diethylamino)sulfur trifluorideHCID 21350204HCID 21350204, compound

Product 1

HCID 21350203HCID 21350203, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3 ml of dichloromethane was added to 0.18 ml of diethylaminosulfur trifluoride. Into the mixture was added dropwise a solution of 3 ml of dichloromethane containing 371 mg of 2-benzyl-3-methoxymethyloxy-6-[(3R)-3-hydroxy-2-pyrrolidinone-1-yl]pyridine under cooling in an ethanol/dry ice bath. The mixture was returned to room temperature and stirred for 2 hours. Then, water was added thereto, and the mixture was extracted with ethyl acetate. The organic phase was further washed with brine, dried over anhydrous sodium sulfate and the solvents was removed. The residue was subjected to silica gel column chromatography using 17-20% ethyl acetate/hexane as an eluent for separation and purification, to give 116 mg of the target compound.

Workup

  1. temperatureunder cooling in an ethanol/dry ice bath
  2. customwas returned to room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic phase was further washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvents was removed
  7. customfor separation and purification

Sources & evidence

ORD record
ord-3033169cdf7343f088df80a793e76baa
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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