Hydrochloric Acid → HCID 67381033, compound

HRID 1804169Notes

Reaction equation

[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]1[CH:23]=[CH:22][C:17]([C:18](OC)=[O:19])=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl.[CH3:27][C:28]1[CH:33]=[C:32]([CH3:34])[CH:31]=[CH:30][C:29]=1[N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>O1CCOCC1.CO>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]1[CH:15]=[CH:16][C:17]([C:18]([N:38]2[CH2:39][CH2:40][N:35]([C:29]3[CH:30]=[CH:31][C:32]([CH3:34])=[CH:33][C:28]=3[CH3:27])[CH2:36][CH2:37]2)=[O:19])=[CH:22][CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To methyl (R)-4-(4-benzyl-2-oxooxazolidin-3-yl)benzoate (0.19 g) described in Preparation Example 22 were added 1N aqueous sodium hydroxide solution (0.92 mL), methanol (5 mL) and 1,4-dioxane (1 mL), and the mixture was stirred at 65° C. for 7 hr. 1N hydrochloric acid (0.92 mL) was added, 1-(2,4-dimethylphenyl)piperazine (0.116 g) and 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (0.17 g) were added, and the mixture was stirred at room temperature. After completion of the reaction, the mixture was extracted with ethyl acetate, washed with saturated brine, and the solvent was evaporated. The residue was purified by column chromatography (chloroform) to give the title compound (175.4 mg).

Workup

stirringthe mixture was stirred at room temperature
customAfter completion of the reaction
extractionthe mixture was extracted with ethyl acetate
washwashed with saturated brine
customthe solvent was evaporated
customThe residue was purified by column chromatography (chloroform)

Sources & evidence

ORD record: ord-28a3db7a40c34947a4f525dd4d38a4be
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354401B2

Reaction notes

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