4-Methylmorpholine → (R)-3-{4-[4-(2-ethyl-4-methylphenyl)piperazine-1-carbonyl]phenyl}-4-isopropyloxazolidin-2-one

HRID 1804167Notes

Reaction equation

HRID 1804167 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].Cl.[CH2:20]([C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:23]=1[N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[CH3:21].O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.CN1CCOCC1>CO.C(Cl)(Cl)Cl>[CH2:20]([C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:23]=1[N:29]1[CH2:30][CH2:31][N:32]([C:14]([C:13]2[CH:12]=[CH:11][C:10]([N:5]3[C@H:4]([CH:1]([CH3:2])[CH3:3])[CH2:8][O:7][C:6]3=[O:9])=[CH:18][CH:17]=2)=[O:16])[CH2:33][CH2:34]1)[CH3:21]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 58484694(R)-4-(4-isopropyl-2-oxooxazolidin-3-yl)benzoic acidHCID 673810191-(2-Ethyl-4-methylphenyl)piperazine hydrochloride

Product 1

HCID 67381241(R)-3-{4-[4-(2-ethyl-4-methylphenyl)piperazine-1-carbonyl]phenyl}-4-isopropyloxazolidin-2-oneYield 10.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a mixture of (R)-4-(4-isopropyl-2-oxooxazolidin-3-yl)benzoic acid (482 mg) described in Preparation Example 18, 1-(2-ethyl-4-methylphenyl)piperazine hydrochloride (499 mg), which is the intermediate described in Preparation Example 15, and 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (DMT-MM) (829 mg) were added chloroform (3 mL), methanol (3 mL) and N-methylmorpholine (220 μL), 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 (88 mg).

Workup

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

Sources & evidence

ORD record
ord-f5076786e4394f44b59fc41b8ec0235e
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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