Hydrochloric Acid → HCID 67380716, compound

HRID 1804189Notes

Reaction equation

HRID 1804189 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:17]=[CH:16][C:10]([C:11]([O:13]CC)=O)=[CH:9][CH:8]=2)[C@H:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:4][O:3]1.[OH-].[Na+].Cl.[CH3:27][C:28]1[C:29]([N:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)=[N:30][CH:31]=[C:32]([CH3:34])[CH:33]=1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>CO.O1CCOCC1.O>[CH3:27][C:28]1[C:29]([N:35]2[CH2:36][CH2:37][N:38]([C:11]([C:10]3[CH:16]=[CH:17][C:7]([N:6]4[C@H:5]([C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=5)[CH2:4][O:3][C:2]4=[O:1])=[CH:8][CH:9]=3)=[O:13])[CH2:39][CH2:40]2)=[N:30][CH:31]=[C:32]([CH3:34])[CH:33]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 584844961-(3,5-Dimethylpyridin-2-yl)piperazineHCID 58484603HCID 58484603, compound

Product 1

HCID 67380716HCID 67380716, compoundYield 15.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Ethyl (R)-4-(2-oxo-4-phenyl-oxazolidin-3-yl)benzoate (623 mg) described in Preparation Example 75 was dissolve in methanol (3 mL) and 1,4-dioxane (3 mL), 1N aqueous sodium hydroxide solution (5 mL) was added, and the mixture was stirred at room temperature for 3 hr. The mixture was neutralized with 1N hydrochloric acid (5 mL), 1-(3,5-dimethylpyridin-2-yl)piperazine (383 mg) described in Preparation Example 47 and 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (DMT-MM) (829 mg) were added, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was purified by column chromatography (chloroform:methanol) to give the title compound (144 mg).

Workup

  1. additionwere added
  2. stirringthe mixture was stirred at room temperature overnight
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-eec1275132b0409286da41183dad1f79
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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