benzyl 4-(N,N'-bis{[(2-methyl-2-propanyl)oxy]carbonyl}carbamimidoyl)-1-piperazinecarboxylate → [tert-Butoxycarbonylimino(piperazin-1-yl)methyl]carbamic acid tert-butyl ester

HRID 1053826Notes

Reaction equation

HRID 1053826 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C:9]([N:18]1[CH2:23][CH2:22][N:21](C(OCC2C=CC=CC=2)=O)[CH2:20][CH2:19]1)=[N:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:7])([CH3:4])[CH3:3]>C(O)C.[Pd]>[CH3:17][C:14]([O:13][C:11](=[O:12])[NH:10][C:9](=[N:8][C:6](=[O:7])[O:5][C:2]([CH3:4])([CH3:3])[CH3:1])[N:18]1[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]1)([CH3:15])[CH3:16]

Participants

4

Reactant 1

HCID 131736303benzyl 4-(N,N'-bis{[(2-methyl-2-propanyl)oxy]carbonyl}carbamimidoyl)-1-piperazinecarboxylate

Product 1

HCID 68635492[tert-Butoxycarbonylimino(piperazin-1-yl)methyl]carbamic acid tert-butyl esterYield 163.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the compound prepared in Example 27 (0.045 g, 0.056 mmol) in ethanol (10 mL) was added Pd/C (20% by wt, 0.010 g). The reaction was stirred under an atmosphere of hydrogen (40 psi) at room temperature for 2 h. The reaction mixture was filtered through diatomaceous earth and the filtrate concentrated to afford the title compound (0.03 g, 69%) as a pale green solid.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-5325d82b197941b09f79600d4ab6510c
Source dataset
uspto-grants-2016_07
Patent number
US09394250B2

Reaction notes

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