4-Methylmorpholine → (R)-3-{4-[4-(4-chlorobenzoyl)piperidine-1-carbonyl]phenyl}-4-isopropyloxazolidin-2-one

HRID 1803964Notes

Reaction equation

HRID 1803964 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.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[O:28])=[CH:23][CH:22]=1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.CN1CCOCC1>CO.C(Cl)(Cl)Cl>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]([CH:29]2[CH2:34][CH2:33][N:32]([C:14]([C:13]3[CH:12]=[CH:11][C:10]([N:5]4[C@H:4]([CH:1]([CH3:2])[CH3:3])[CH2:8][O:7][C:6]4=[O:9])=[CH:18][CH:17]=3)=[O:16])[CH2:31][CH2:30]2)=[O:28])=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 27771144-(4-Chlorobenzoyl)piperidine hydrochlorideHCID 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 54755003(R)-3-{4-[4-(4-chlorobenzoyl)piperidine-1-carbonyl]phenyl}-4-isopropyloxazolidin-2-oneYield 80.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a mixture of (R)-4-(4-isopropyl-2-oxooxazolidin-3-yl)benzoic acid (499 mg) described in Preparation Example 18, (4-chlorophenyl)piperidin-4-ylmethanone hydrochloride (520 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), 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 (chloroform:methanol) to give the title compound (728 mg).

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was purified by column chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-92b208132c954507a34657e64a25aeb8
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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