Hydrochloric Acid → Ethyl 3,5-dimethyl-4-[[2-methyl-5-(4-oxo-1-piperidyl)benzoyl]amino]benzoate

HRID 239948Notes

Reaction equation

O1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:12]=[CH:13][C:14]([CH3:33])=[C:15]([CH:32]=3)[C:16]([NH:18][C:19]3[C:29]([CH3:30])=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][C:20]=3[CH3:31])=[O:17])[CH2:7][CH2:6]2)[O:4]CC1.Cl>CC(C)=O.O.[OH-].[Na+]>[CH3:31][C:20]1[CH:21]=[C:22]([CH:28]=[C:29]([CH3:30])[C:19]=1[NH:18][C:16](=[O:17])[C:15]1[CH:32]=[C:11]([N:8]2[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]2)[CH:12]=[CH:13][C:14]=1[CH3:33])[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 4-[[5-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-2-methyl-benzoyl]amino]-3,5-dimethyl-benzoate (205 mg, 452.99 μmoles) in acetone (5 ml) is added a mixture of 5M HCl (1 mL) in H2O (1 mL) and heated to 60° C. After 12 hours, the mixture is cooled to ambient temperature, diluted with 2M NaOH to pH 6 and extracted with ethyl acetate. The combined organic layers are dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (silica gel) using 0-40% ethyl acetate in hexane to afford the title compound as an off-white foam (0.11 g, 61%). Mass spectrum (m/z): 409.2 (M+1).

Workup

temperaturethe mixture is cooled to ambient temperature
extractionextracted with ethyl acetate
dry with materialThe combined organic layers are dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe resulting residue is purified by flash chromatography (silica gel)

Sources & evidence

ORD record: ord-30dd5f52bdb74d6d8d520f1790e4019a
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642768B2

Reaction notes

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