Sodium hydride → 2,2-dimethylpropyl 4-(4-[5-[(1S)-1-hydroxyethyl]-1,2,4-oxadiazol-3-yl]pyridin-2-yl)-1-piperazinecarboxylate

HRID 421822Notes

Reaction equation

[NH2:1][C:2](=[N:23][OH:24])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:16])[CH2:11][CH2:10]2)[CH:4]=1.[H-].[Na+].[C:27](OC)(=O)[C@H:28]([CH3:30])[OH:29].[Cl-].[NH4+]>O1CCCC1>[OH:29][C@H:28]([C:30]1[O:24][N:23]=[C:2]([C:3]2[CH:8]=[CH:7][N:6]=[C:5]([N:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:16])[CH2:11][CH2:10]3)[CH:4]=2)[N:1]=1)[CH3:27]

Participants

Conditions

Temperature: 60 °C

Procedure

2,2-Dimethylpropyl 4-{4-[amino(hydroxyimino)methyl]pyridin-2-yl}-1-piperazinecarboxylate (657 mg) was dissolved in tetrahydrofuran (10 mL), oily sodium hydride (82.6 mg) was added thereto and stirred at 60° C. for 15 minutes, then methyl (S)-lactate (0.333 mL) was added thereto and heated under reflux for 1 hour. Aqueous saturated ammonium chloride solution was added to the reaction liquid, and extracted with ethyl acetate. The organic layer was washed with saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away, and the resulting residue was isolated and purified through silica gel column chromatography (hexane/ethyl acetate=1/1) to obtain 402 mg of the entitled compound as a colorless solid.

Workup

temperatureheated
temperatureunder reflux for 1 hour
extractionextracted with ethyl acetate
washThe organic layer was washed with saturated saline water
dry with materialdried with anhydrous sodium sulfate
customThe solvent was evaporated away
customthe resulting residue was isolated
custompurified through silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record: ord-1c7c403979834b1bba20428783564d99
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101618B2

Reaction notes

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