1-(2-Hydroxyethyl)piperazine → HCID 67612520, compound

HRID 727671Notes

Reaction equation

HRID 727671 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.[OH:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>C(#N)C>[OH:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][N:26]([C:1]([C@@H:4]2[CH2:8][C@H:7]([S:9][CH2:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[CH2:6][N:5]2[CH3:19])=[O:3])[CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 15297072HCID 15297072, compound

Product 1

HCID 67612520HCID 67612520, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

800 mg of N,N'-carbonyldiimidazole were added to a suspension of 1.13 g of (2S,4S)-2-carboxy-4-(4-methoxybenzylthio)-1-methylpyrrolidine in 20 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 600 mg of N-hydroxyethylpiperazine were added to the mixture. The temperature was allowed to rise to room temperature over a period of 30 minutes. The reaction mixture was then concentrated by evaporation under reduced pressure, and the residue was purified by reverse phase column chromatography using LiChroprep RP-8 (trade mark) as the stationary phase and 70% v/v aqueous methanol as the eluent, to give 1160 mg of the title compound as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-92a1f4bce22b4f7dad7524b5cffef506
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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