Piperazine → 1,1-dimethylethyl [(1S)-3-methyl-1-(1-piperazinylcarbonyl)butyl]carbamate

HRID 870781Notes

Reaction equation

HRID 870781 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:10](=[O:12])[N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 10868DicyclohexylcarbodiimideHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-

Product 1

HCID 598683411,1-dimethylethyl [(1S)-3-methyl-1-(1-piperazinylcarbonyl)butyl]carbamateYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 1.00 g (4.33 mmol) of (S)-2-((tert-butoxycarbonyl)amino)-4-methylpentanoic acid was added 750 mg (8.66 mmol) of piperazine, 20 mL of DCM, 1.34 g (6.5 mmol) of DCC and 17.9 mL (12.99 mmol) of TEA. This was allowed to stir overnight at room temperature. The next morning, it was diluted with more DCM, and filtered. The filtrate was concentrated and purified in the ISCO using a 40 gram column and eluting with 0-10% MeOH/DCM to obtain the desired product in 79% yield.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. custompurified in the ISCO
  4. washeluting with 0-10% MeOH/DCM

Sources & evidence

ORD record
ord-aca8d526467f4a878ebe12555648492d
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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