Sodium Azide → HCID 86663856, compound

HRID 1022625Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][C@H:9]2[CH2:22]OS(C)(=O)=O)=[CH:4][C:3]=1[F:28].[N-:29]=[N+:30]=[N-:31].[Na+]>CN(C=O)C>[N:29]([CH2:22][C@H:9]1[C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([F:28])[CH:4]=2)[O:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]1)=[N+:30]=[N-:31]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of tert-butyl (6S,7R)-7-(4-chloro-3-fluorophenyl)-6-{[(methylsulfonyl)oxy]methyl}-1,4-oxazepane-4-carboxylate (4.00 g) in DMF (46 mL) was added sodium azide (891 mg), and the mixture was stirred at 70° C. overnight. To the reaction mixture was added distilled water, and the mixture was extracted with ethyl acetate. The extract was washed with distilled water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel filtration to give the title compound (6.76 g).

Workup

additionTo the reaction mixture was added
distillationdistilled water
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with distilled water and brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
filtrationThe residue was purified by silica gel filtration

Sources & evidence

ORD record: ord-4438469abda442348d4a1bf772494d66
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722662B2

Reaction notes

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