Acetic Acid → HCID 20342250, compound

HRID 2050192Notes

Reaction equation

HRID 2050192 reaction equation
[OH:1][CH:2]([CH:6]1[CH2:11][N:10]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][CH2:8][N:7]1[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:3]([OH:5])=[O:4].[N+](=[CH2:28])=[N-].C(O)(=O)C>CO.CCOCC>[OH:1][CH:2]([CH:6]1[CH2:11][N:10]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][CH2:8][N:7]1[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:3]([O:5][CH3:28])=[O:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 9550Diazomethane2×HCID 20342253HCID 20342253, compound

Product 1

HCID 20342250HCID 20342250, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 452 mg of 2-hydroxy-2-(1,4-dibenzylpiperazin-2-yl)acetic acid in 5 ml of methanol is added a solution of diazomethane in ether. After the excess amount of diazomethane is decomposed with acetic acid, the mixture is evaporated to dryness under reduced pressure. The residue is dissolved in ether. The resulting solution is washed with 10% aqueous sodium sulfate and water, dried over sodium sulfate and evaporated under reduced pressure to yield 468 mg of methyl 2-hydroxy-2-(1,4-dibenzylpiperazin-2-yl)acetate as a mixture of erythro and threo.

Workup

  1. customthe mixture is evaporated to dryness under reduced pressure
  2. dissolutionThe residue is dissolved in ether
  3. washThe resulting solution is washed with 10% aqueous sodium sulfate and water
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-715c1874457546a583f3215b731a9b89
Source dataset
uspto-grants-1980_04
Patent number
US04200628

Reaction notes

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