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

HRID 388454Notes

Reaction equation

HRID 388454 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7])([O-:3])=[O:2].Cl.[CH3:14][O:15][C:16](=[O:26])[CH2:17][C:18]1([CH2:24][NH2:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.CCN(C(C)C)C(C)C>ClCCl>[CH3:14][O:15][C:16](=[O:26])[CH2:17][C:18]1([CH2:24][NH:25][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 118752-Nitrobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 45260937Methyl 2-[1-(aminomethyl)cyclohexyl]acetate hydrochloride

Product 1

HCID 68725102{1-[(2-Nitro-benzoylamino)-methyl]-cyclohexyl}-acetic acid methyl esterYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-nitrobenzoyl chloride (0.3 mL, 2.05 mmol) and (1-aminomethyl-cyclohexyl)-acetic acid methyl ester hydrochloride (500 mg, 2.25 mmol) (prepares according to example A) in dichloromethane (10 mL) is added DIPEA (0.75 mL, 4.02 mmol). The mixture is stirred at room temperature for 16 hours. The reaction mixture is concentrated and the resulting residue is purified by flash chromatography with 50% EtOAc in Hexane as the eluent to afford the desired {1-[(2-nitro-benzoylamino)-methyl]-cyclohexyl}-acetic acid methyl ester (680 mg, 99%).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customthe resulting residue is purified by flash chromatography with 50% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-a7246f792cc84d279f76f489d3951dbe
Source dataset
uspto-grants-2013_02
Patent number
US08377949B2

Reaction notes

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