Water → HCID 53906472, compound

HRID 975661Notes

Reaction equation

HRID 975661 reaction equation
CC(C)([O-])C.[C:6]([OH:9])(=[S:8])[CH3:7].[CH2:10]([O:13][C:14]([N:16]1[CH2:20][C@H:19](OS(C)(=O)=O)[CH2:18][C@H:17]1[CH2:26][N:27]1[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][C:28]1=[O:34])=[O:15])[CH:11]=[CH2:12].O>CN(C)C=O>[C:6]([S:8][C@@H:19]1[CH2:20][N:16]([C:14]([O:13][CH2:10][CH:11]=[CH2:12])=[O:15])[C@H:17]([CH2:26][N:27]2[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][C:28]2=[O:34])[CH2:18]1)(=[O:9])[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 45749132-Methylpropan-2-olateHCID 56998705HCID 56998705, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 53906472HCID 53906472, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of pottasium t-butoxide (1.24 g) in N,N-dimethylformamide (15 ml) was dropwise added thioacetic acid (0.85 ml) under ice cooling with stirring. The mixture was stirred at the same temperature for 30 minutes. To the solution of (2S,4R)-1-allyloxycarbonyl-2-(2-oxo-4-methylpiperazin-1-yl) methyl-4-(methanesulfonyloxy)pyrrolidine (3.19 g) in N,N-dimethylformamide (15 ml) was added the mixture obtained above at ambient temperature with stirring. The mixture was stirred at 80°-90° C. for 1.5 hours. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of chloroform and methanol (20:1 v/v) to give (2S,4S)-4-acetylthio-1-allyloxycarbonyl-2-(2-oxo-4-methylpiperazin-1-yl) methylpyrrolidine (3.24 g).

Workup

  1. stirringThe mixture was stirred at the same temperature for 30 minutes
  2. customobtained above at ambient temperature
  3. stirringwith stirring
  4. stirringThe mixture was stirred at 80°-90° C. for 1.5 hours
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was purified by silica gel column chromatography
  10. washeluting with a mixture of chloroform and methanol (20:1 v/v)

Sources & evidence

ORD record
ord-0f0749e4929f4eb6817d12b3f4378f95
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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