Sodium Azide → HCID 22242898, compound

HRID 891735Notes

Reaction equation

CS(O[CH:6]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[CH2:7]1)(=O)=O.[N-:23]=[N+:24]=[N-:25].[Na+]>CN(C)C=O>[N:23]([CH:6]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[CH2:7]1)=[N+:24]=[N-:25]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-methanesulfonyloxy-1-(p-nitrobenzyloxycarbonyl)azetidine (4.63 g, 14.0 mmol) (obtained as described in Reference Example 54(2)) in dimethylformamide (140 ml) was added sodium azide (1.37 g, 21.0 mmol), and the mixture was stirred in an oil bath (100° C.) for 4 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (2:1→1:1) as the eluant to afford 3-azido-1-(p-nitrobenzyloxycarbonyl)azetidine (2.15 g, yield 55%) as pale yellow crystals.

Workup

customthe completion of the reaction
customthe reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution
washThe organic layer was washed with saturated aqueous sodium chloride solution
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record: ord-e7bc774f853649a788db06976045a7a6
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07001897B2

Reaction notes

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