4-[2-(2-{[2-(Tert-butoxycarbonyl-methyl-amino)-acetyl]-methyl-amino}-acetoxy)-4-methyl-pentanoyl]-piperazine-1-carboxylic acid benzyl ester → {[2-(Tert-butoxycarbonyl-methyl-amino)-acetyl]-methyl-amino}-acetic acid 3-methyl-1-(piperazine-1-carbonyl)-butyl ester

HRID 2062253Notes

Reaction equation

HRID 2062253 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:41])[CH:18]([O:23][C:24](=[O:40])[CH2:25][N:26]([C:28](=[O:39])[CH2:29][N:30]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH3:31])[CH3:27])[CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>CO.[Pd]>[CH3:21][CH:20]([CH3:22])[CH2:19][CH:18]([O:23][C:24](=[O:40])[CH2:25][N:26]([C:28](=[O:39])[CH2:29][N:30]([C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33])[CH3:31])[CH3:27])[C:17]([N:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1)=[O:41]

Participants

4

Reactant 1

HCID 670984054-[2-(2-{[2-(Tert-butoxycarbonyl-methyl-amino)-acetyl]-methyl-amino}-acetoxy)-4-methyl-pentanoyl]-piperazine-1-carboxylic acid benzyl ester

Product 1

HCID 67099091{[2-(Tert-butoxycarbonyl-methyl-amino)-acetyl]-methyl-amino}-acetic acid 3-methyl-1-(piperazine-1-carbonyl)-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 4-[2-(2-{[2-(tert-butoxycarbonyl-methyl-amino)-acetyl]-methyl-amino}-acetoxy)-4-methyl-pentanoyl]-piperazine-1-carboxylic acid benzyl ester (208 mg, 0.49 mmol) in 1.6 mL of methanol was added 70 mg of Pd/C (10% wt Pd on carbon). The reaction mixture was hydrogenated using a balloon of H2 for 4 h at room temperature. The mixture was then filtered through Celite, and the solvent removed to give {[2-(tert-butoxycarbonyl-methyl-amino)-acetyl]-methyl-amino}-acetic acid 3-methyl-1-(piperazine-1-carbonyl)-butyl ester.

Workup

  1. customfor 4 h
  2. customat room temperature
  3. filtrationThe mixture was then filtered through Celite
  4. customthe solvent removed

Sources & evidence

ORD record
ord-2e812de0fb1c4ec5955416446f7c1902
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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