tert-Butyl piperazine-1-carboxylate → HCID 54491093, compound

HRID 1058582Notes

Reaction equation

HRID 1058582 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])(C)(C)C.C([O:18][C:19](=[O:38])[C@H:20]([CH2:34][CH:35]([CH3:37])[CH3:36])[NH:21]C(OC1C=CC([N+]([O-])=O)=CC=1)=O)(C)(C)C>CN(C=O)C>[N:8]1([C:6]([NH:21][C@H:20]([C:19]([OH:38])=[O:18])[CH2:34][CH:35]([CH3:37])[CH3:36])=[O:7])[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 53888372HCID 53888372, compound

Product 1

HCID 54491093HCID 54491093, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-(tert-butoxycarbonyl)piperazine (60 mg, 0.036 mmol) and N-(4-nitrophenoxycarbonyl)-L-leucine tert-butyl ester (128 mg, 0.36 mmol) in DMF was stirred at 60° C. for 1 h. concentrated in vacuo and the residue treated with 4 M HCl in dioxane (5 ml) for 16 h. The mixture was concentrated in vacuo, azeotroped with toluene and treated with 4 M HCl in dioxane (5 ml) for 16 h. The mixture was concentrated in vacuo to afford the title compound.

Workup

  1. concentrationconcentrated in vacuo
  2. additionthe residue treated with 4 M HCl in dioxane (5 ml) for 16 h
  3. concentrationThe mixture was concentrated in vacuo
  4. customazeotroped with toluene
  5. additiontreated with 4 M HCl in dioxane (5 ml) for 16 h
  6. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-e0f98c56286b4d26b2a839a148d49f87
Source dataset
uspto-grants-2003_02
Patent number
US06518267B1

Reaction notes

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