HCID 69286135, compound → HCID 69284649, compound

HRID 2225243Notes

Reaction equation

HRID 2225243 reaction equation
FC(F)(F)C(O)=O.[CH:8]([C@@H:11]1[CH2:16][C@H:15]([N:17]([CH:19]([CH3:21])[CH3:20])[CH3:18])[CH2:14][CH2:13][C@@H:12]1[NH:22][C:23](=[O:36])[CH2:24][NH:25]C(=O)OCC1C=CC=CC=1)([CH3:10])[CH3:9]>CO.[Pd]>[NH2:25][CH2:24][C:23]([NH:22][C@H:12]1[CH2:13][CH2:14][C@@H:15]([N:17]([CH:19]([CH3:20])[CH3:21])[CH3:18])[CH2:16][C@H:11]1[CH:8]([CH3:10])[CH3:9])=[O:36]

Participants

4

Reactant 1

HCID 69286135HCID 69286135, compound

Product 1

HCID 69284649HCID 69284649, compoundYield 122.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of benzyl 2-((1S,2S,4R)-2-isopropyl-4-(isopropyl(methyl)amino)cyclohexylamino)-2-oxoethylcarbamate trifluoroacetate (188 mg) in MeOH (10 mL) was charged with 10% Pd/C, Degussa (30 mg). The reaction flask was evacuated and then back-filled with hydrogen; this was repeated three more times. The reaction was stirred under 1 atm of H2 for 3 h and then filtered and concentrated to afford 2-amino-N-((1S,2S,4R)-2-isopropyl-4-(isopropyl(methyl)amino)cyclohexyl)acetamide (120 mg). MS found: (M+H)+=270.3.

Workup

  1. customThe reaction flask was evacuated
  2. additionback-filled with hydrogen
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f97ed4431918492f9edfe230f1194fe0
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

Loading…