{1-[(2-Nitro-benzoylamino)-methyl]-cyclohexyl}-acetic acid methyl ester → {1-[(2-Amino-benzoylamino)-methyl]-cyclohexyl}-acetic acid methyl ester

HRID 388455Notes

Reaction equation

HRID 388455 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1([CH2:11][NH:12][C:13](=[O:23])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-])=O)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>CCO.[Pd]>[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1([CH2:11][NH:12][C:13](=[O:23])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH2:20])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

4

Reactant 1

HCID 68725102{1-[(2-Nitro-benzoylamino)-methyl]-cyclohexyl}-acetic acid methyl ester

Product 1

HCID 68724696{1-[(2-Amino-benzoylamino)-methyl]-cyclohexyl}-acetic acid methyl esterYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of {1-[(2-nitro-benzoylamino)-methyl]-cyclohexyl}-acetic acid methyl ester (680 mg, 2.03 mmol), 10% Pd/C (120 mg) in EtOH (25 mL) is stirred under H2 atmosphere at room temperature for 16 hours. The reaction mixture is filtered and the organic layer is concentrated to give the desired {1-[(2-amino-benzoylamino)-methyl]-cyclohexyl}-acetic acid methyl ester (619 mg, 100%).

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe organic layer is concentrated

Sources & evidence

ORD record
ord-66ea606a6d8347a7a931e86584dae720
Source dataset
uspto-grants-2013_02
Patent number
US08377949B2

Reaction notes

Loading…