Chloroform → (R)-4-isopropyl-3-[4-(4-p-tolyloxypiperidine-1-carbonyl)phenyl]oxazolidin-2-one

HRID 1804179Notes

Reaction equation

HRID 1804179 reaction equation
[CH:1]([C@@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=1)([CH3:3])[CH3:2].[C:19]1([CH3:32])[CH:24]=[CH:23][C:22]([O:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:21][CH:20]=1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.C(Cl)(Cl)Cl>CO>[CH:1]([C@@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:10]1[CH:11]=[CH:12][C:13]([C:14]([N:29]2[CH2:30][CH2:31][CH:26]([O:25][C:22]3[CH:23]=[CH:24][C:19]([CH3:32])=[CH:20][CH:21]=3)[CH2:27][CH2:28]2)=[O:16])=[CH:17][CH:18]=1)([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 38374974-(4-Methylphenoxy)piperidineHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 58484694(R)-4-(4-isopropyl-2-oxooxazolidin-3-yl)benzoic acid

Product 1

HCID 67380846(R)-4-isopropyl-3-[4-(4-p-tolyloxypiperidine-1-carbonyl)phenyl]oxazolidin-2-oneYield 23.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of (R)-4-(4-isopropyl-2-oxooxazolidin-3-yl)benzoic acid (499 mg) described in Preparation Example 18, 4-(p-tolyloxy)piperidine (383 mg) and 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (DMT-MM) (829 mg) were added chloroform (3 mL) and methanol (3 mL), and the mixture was stirred at room temperature overnight. After evaporation of the solvent, the residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (196 mg).

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was purified by column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-746be08133ea47d7ba390b4866ca8402
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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