Methyl iodide → (S)-2-Methoxycarbonylmethyl-piperazine-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

HRID 1963068Notes

Reaction equation

HRID 1963068 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@@H:13]([CH2:24][C:25]([OH:27])=[O:26])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[C:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:12][C@@H:13]1[CH2:24][C:25]([O:27][CH3:28])=[O:26])=[O:18])([CH3:22])([CH3:23])[CH3:21]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 68205818[(S)-4-Benzyloxycarbonyl-1-tert-butoxycarbonyl-piperazin-2-yl]-acetic acid

Product 1

HCID 67772911(S)-2-Methoxycarbonylmethyl-piperazine-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl esterYield 89.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of the compound of step 1 (2.52 g, 6.66 mmol) in 45 ml of acetone were added potassium carbonate (5.522 g, 39.96 mmol) and iodomethane (1.24 ml, 19.98 mmol) and the solution was stirred at room temperature overnight. The mixture was filtered and the filtrate was concentrated to dryness. The residue was dissolved in EA, washed twice with brine, dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by chromatography on silica gel (cyclohexane/EA, 100:0, then 85:15) to give 2.334 g of the title compound as a colorless oil.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness
  3. dissolutionThe residue was dissolved in EA
  4. washwashed twice with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by chromatography on silica gel (cyclohexane/EA, 100:0

Sources & evidence

ORD record
ord-449a547b11ce4819919a2983f7b03f26
Source dataset
uspto-grants-2013_04
Patent number
US08415336B2

Reaction notes

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