tert-Butyl piperazine-1-carboxylate → Methyl 2-Carbobenzyloxyamino-3-(4-tert-butoxycarbonylpiperazin-1-yl)propionate

HRID 991757Notes

Reaction equation

HRID 991757 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4](=[CH2:16])[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>C(#N)C.CO>[C:6]([NH:5][CH:4]([CH2:16][N:28]1[CH2:27][CH2:26][N:25]([C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:24])[CH2:30][CH2:29]1)[C:3]([O:2][CH3:1])=[O:17])([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

Participants

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 3525700Z-Dehydro-Ala-OMe

Product 1

HCID 21940471Methyl 2-Carbobenzyloxyamino-3-(4-tert-butoxycarbonylpiperazin-1-yl)propionate

Reagents, catalysts & solvents 1

HCID 21959252Acetonitrile methanolSolvent

Procedure

To N-carbobenzyloxydehydroalanine methyl ester (2.0 g, 8.4 mmol) was added 4-tert-butoxycarbonylpiperazine (1.56 g, 1.0 eq), ferric chloride (0.220 g, 0.2 eq) in a 6:1 mixture of acetonitrile/methanol. The reaction mixture was stirred at room temperature for 2 days. The reaction mixture was evaporated under reduced pressure. EtOAc was added and the organic layer washed with a soldium sulfate solution. Upon removal of the solvent under reduced pressure, the crude material was purified by column chromatography (silica gel; CH2Cl2:MeOH 4:1) to afford the title compound.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. additionEtOAc was added
  3. washthe organic layer washed with a soldium sulfate solution
  4. customUpon removal of the solvent under reduced pressure
  5. customthe crude material was purified by column chromatography (silica gel; CH2Cl2:MeOH 4:1)

Sources & evidence

ORD record
ord-38e2d27f06a941b6b4b0f71a0b201dbd
Source dataset
uspto-grants-2002_10
Patent number
US06465513B1

Reaction notes

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