Hydrogen chloride-ethyl acetate → HCID 71252246, compound

HRID 2411577Notes

Reaction equation

HRID 2411577 reaction equation
[CH3:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:27][CH2:26][CH2:25][S:24]4(=[O:29])=[O:28])=[CH:19][C:18]=3[N:30]3[CH2:34][CH2:33][O:32][C:31]3=[O:35])=[O:16])[CH2:11][CH2:10]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[ClH:36].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:36].[CH3:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:27][CH2:26][CH2:25][S:24]4(=[O:28])=[O:29])=[CH:19][C:18]=3[N:30]3[CH2:34][CH2:33][O:32][C:31]3=[O:35])=[O:16])[CH2:11][CH2:10]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 71252247HCID 71252247, compound

Product 1

HCID 71252246HCID 71252246, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To methyl 4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)-2-(2-oxooxazolidin-3-yl)benzoate (170 mg) described in Preparation Example 32 were added methanol (2.5 mL) and 1N aqueous sodium hydroxide solution (0.75 mL), and the mixture was stirred at 60° C. After completion of the reaction, the reaction mixture was neutralized with 1N hydrochloric acid (0.75 mL), 1-(3,5-dimethylpyridin-2-yl)piperazine (96 mg) described in Preparation Example 79 and 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (138 mg) were added, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, the mixture was extracted with ethyl acetate, and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (ethyl acetate:methanol) to give 3-{2-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]-5-(1,1-dioxo-1λ6-isothiazolidin-2-yl)phenyl}oxazolidin-2-one. The obtained 3-{2-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]-5-(1,1-dioxo-1λ6-isothiazolidin-2-yl)phenyl}oxazolidin-2-one was dissolved in ethyl acetate, 4N hydrogen chloride/ethyl acetate (0.13 mL) was added, and the precipitate was collected by filtration to give the title compound (131 mg).

Workup

  1. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-4bc81af8dbc54609bd433861aec2b8dd
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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