Dimethylformamide → HCID 89551301, compound

HRID 340498Notes

Reaction equation

C([O-])(=O)C.[Na+].[N-:6]=[N+:7]=[N-:8].[Na+].CN(C=O)C.[C:15]([O:19][C:20]([NH:22][C@@H:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])[CH2:25][C@H:24]1OS(C)(=O)=O)=[O:21])([CH3:18])([CH3:17])[CH3:16]>O>[N:6]([C@H:28]1[C@@H:23]([NH:22][C:20]([O:19][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:21])[CH2:24][CH2:25][N:26]([C:29]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[O:30])[CH2:27]1)=[N+:7]=[N-:8]

Participants

Conditions

Temperature: 80 °C

Procedure

Sodium acetate (204 mg) and sodium azide (161 mg) were added to a DMF (5 mL) solution containing (trans)-benzyl 4-((tert-butoxycarbonyl)amino)-3-((methylsulfonyl)oxy)piperidin-1-carboxylate (532 mg), followed by stirring at 80° C. for 4 hours. The pH of the reaction solution was adjusted to pH 12 with the addition of water and a 2M sodium hydroxide aqueous solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous sodium sulfate, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1 to 2:1), and a white solid of (cis)-benzyl 3-azido-4-((tert-butoxycarbonyl)amino)piperidin-1-carboxylate (124 mg) was thus obtained.

Workup

extractiona 2M sodium hydroxide aqueous solution, followed by extraction with ethyl acetate
washThe organic layer was washed with saturated saline
dry with materialdried over anhydrous sodium sulfate
distillationthe solvent was distilled away under reduced pressure
customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1 to 2:1)

Sources & evidence

ORD record: ord-a550f1711e72423eb138e442f7074ccd
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895585B2

Reaction notes

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