HCID 69285791, compound → HCID 69286047, compound

HRID 2225272Notes

Reaction equation

HRID 2225272 reaction equation
C(OC([NH:11][CH2:12][C:13]([NH:15][C@H:16]1[CH2:21][CH2:20][C@@H:19]([N:22]([CH:30]([CH3:32])[CH3:31])[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:18][C@H:17]1[CH2:33][OH:34])=[O:14])=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][CH2:12][C:13]([NH:15][C@H:16]1[CH2:21][CH2:20][C@@H:19]([N:22]([CH:30]([CH3:31])[CH3:32])[C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:28])[CH3:27])[CH2:18][C@H:17]1[CH2:33][OH:34])=[O:14]

Participants

4

Reactant 1

HCID 69285791HCID 69285791, compound

Product 1

HCID 69286047HCID 69286047, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl(1R,3R,4S)-4-(2-Benzyloxycarbonylamino-acetylamino)-3-(hydroxymethyl)cyclohexyl(isopropyl)carbamate (2.2 g, 0.0046 mol), in 30 mL of MeOH was treated with 1 g of 10% Pd/C and hydrogenated overnight at 55 psi. The mixture was filtered through Celite and concentrated on a rotary evaporator to give tert-butyl(1R,3R,4S)-4-(2-aminoacetamido)-3-(hydroxymethyl)cyclohexyl-(isopropyl)carbamate as a white solid. This was used without further purification.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-0679c93e847045b894ca0008b51797c0
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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