Sodium Chloride → (S)-4-Benzyl 1-tert-butyl 2-ethyl piperazine-1,2,4-tricarboxylate

HRID 1006348Notes

Reaction equation

HRID 1006348 reaction equation
C(O)(=O)[C@H]([C@@H](C(O)=O)O)O.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][C@H:19]1[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:17])([CH3:14])([CH3:13])[CH3:12].C(=O)(O)[O-].[Na+].Cl[C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36].[Cl-].[Na+]>O1CCCC1.O.C(OCC)(=O)C>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][N:21]([C:35]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[O:36])[CH2:20][C@H:19]1[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 86589649(2S)-2-ethoxycarbonylpiperazine-1-carboxylic acid 1-tert-butyl ester D-tartarate

Product 1

HCID 59016652(S)-4-Benzyl 1-tert-butyl 2-ethyl piperazine-1,2,4-tricarboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S)-2-ethoxycarbonylpiperazine-1-carboxylic acid 1-tert-butyl ester D-tartarate (9.56 g) in tetrahydrofuran (90 ml) and water (90 ml) was added sodium bicarbonate (7.87 g) under ice-cooling. Benzyl chloroformate (4.01 ml) was added dropwise to the solution over 2 minutes at the same temperature, and stirred at room temperature for 15 minutes. Ethyl acetate (60 ml) and sodium chloride (5 g) was added to the mixture. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated under reduced pressure to give (2S)-2-ethoxycarbonylpiperazine-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester (10.4 g) as a colorless oil.

Workup

  1. temperaturecooling
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b7d0afa322964a468c2aae6915b222d7
Source dataset
uspto-grants-2004_09
Patent number
US06787543B2

Reaction notes

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