(R)-cyclohexyl-(2-nitro-benzoylamino)-acetic acid methyl ester → (R)-(2-amino-benzoylamino)-cyclohexyl-acetic acid methyl ester

HRID 388447Notes

Reaction equation

HRID 388447 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C@@H:4]([CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[NH:5][C:6](=[O:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-])=O>CCO.[Pd]>[CH3:1][O:2][C:3](=[O:23])[C@H:4]([NH:5][C:6](=[O:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH2:13])[CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

4

Reactant 1

HCID 68726619(R)-cyclohexyl-(2-nitro-benzoylamino)-acetic acid methyl ester

Product 1

HCID 68728963(R)-(2-amino-benzoylamino)-cyclohexyl-acetic acid methyl esterYield 102.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (R)-cyclohexyl-(2-nitro-benzoylamino)-acetic acid methyl ester (1.16 g, 3.62 mmol), 10% Pd/C (250 mg) in EtOH (25 mL) are stirred under H2 atmosphere at room temperature for 16 hours. The reaction mixture is filtered and the organic layer is concentrated to give (R)-(2-amino-benzoylamino)-cyclohexyl-acetic acid methyl ester (1.08 g, 98%).

Workup

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

Sources & evidence

ORD record
ord-45c0417be1c5470b8374183af5f8dde1
Source dataset
uspto-grants-2013_02
Patent number
US08377949B2

Reaction notes

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