1,2-Dichloroethane → N-[4-(oxazolidin-3-ylcarbonyl)phenyl]-2-(2-methylphenyl)-2-(4-chlorophenylamino-carbonylamino)-acetamide

HRID 2244998Notes

Reaction equation

HRID 2244998 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([NH:12][C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)=[O:14])[C:9]([OH:11])=O.[O:23]1[CH2:27][CH2:26][N:25]([C:28]([C:30]2[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=2)=[O:29])[CH2:24]1.C(Cl)CCl>CN(C=O)C>[O:23]1[CH2:27][CH2:26][N:25]([C:28]([C:30]2[CH:35]=[CH:34][C:33]([NH:36][C:9](=[O:11])[CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH3:1])[NH:12][C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[O:14])=[CH:32][CH:31]=2)=[O:29])[CH2:24]1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 686898412-(2-Methylphenyl)-2-(4-chlorophenylaminocarbonylamino)-acetic acidHCID 686942914-(3-Oxazolidinylcarbonyl)phenylamine

Product 1

HCID 11540487N-[4-(oxazolidin-3-ylcarbonyl)phenyl]-2-(2-methylphenyl)-2-(4-chlorophenylamino-carbonylamino)-acetamideYield 31.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-methylphenyl)-2-(4-chlorophenylaminocarbonylamino)-acetic acid (44 mg, 0.14 mmol) and 4-(oxazolidin-3-ylcarbonyl)phenylamine (25 mg, 0.13 mmol) in DMF (3 mL), EDC (75 mg, 0.39 mmol) was added. The reaction mixture was stirred at room temperature overnight. It was then concentrated in vacuo. The residue was purified by HPLC to give the titled compound as a white powder (20 mg). MS 493.2 and 495.2 (M+H, Cl pattern).

Workup

  1. concentrationIt was then concentrated in vacuo
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-9b14bbba324b431b9b081d99eee70da7
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Reaction notes

Loading…