1-Methylpiperazine → HCID 57068274, compound

HRID 362062Notes

Reaction equation

HRID 362062 reaction equation
[C:1]([C@@H:4]1[CH2:8][C@H:7]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH2:6][N:5]1[CH3:19])([OH:3])=O.[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>C(#N)C>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][S:9][C@@H:7]2[CH2:6][N:5]([CH3:19])[C@H:4]([C:1]([N:24]3[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]3)=[O:3])[CH2:8]2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 15297072HCID 15297072, compound

Product 1

HCID 57068274HCID 57068274, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

700 mg of N,N'-carbonyldiimidazole were added to a suspension of 1.0 g of (2S,4S)-2-carboxy-4-(4-methoxybenzylthio)-1-methylpyrrolidine in 15 ml of dry acetonitrile, and the resulting mixture was stirred at 40° C. for 30 minutes. At the end of this time, the reaction mixture was ice-cooled, and 440 μl of N-methylpiperazine were added to the mixture. The temperature was then allowed to rise to room temperature over a period of 30 minutes. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the residue was purified by reverse phase column chromatography using LiChroprep RP-8 (trade mark) as stationary phase and 70% v/v aqueous methanol as the eluent, to give 1060 mg of the title compound as an oil.

Workup

  1. temperaturecooled
  2. waitto rise to room temperature over a period of 30 minutes
  3. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  4. customthe residue was purified by reverse phase column chromatography

Sources & evidence

ORD record
ord-34a9b0cc886244d69e9d4f249602758f
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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