Tributyltin azide → HCID 178452468, compound

HRID 1022716Notes

Reaction equation

C([Sn]([N:14]=[N+:15]=[N-:16])(CCCC)CCCC)CCC.[C:17]([C:19]1[C:20](=[O:48])[N:21]([CH2:25][C@H:26]2[C@H:32]([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([Cl:40])[CH:34]=3)[O:31][CH2:30][CH2:29][N:28]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:27]2)[CH:22]=[CH:23][CH:24]=1)#[N:18]>C1(C)C=CC=CC=1>[Cl:40][C:35]1[CH:34]=[C:33]([C@@H:32]2[O:31][CH2:30][CH2:29][N:28]([C:41]([O:43][C:44]([CH3:45])([CH3:47])[CH3:46])=[O:42])[CH2:27][C@H:26]2[CH2:25][N:21]2[CH:22]=[CH:23][CH:24]=[C:19]([C:17]3[NH:16][N:15]=[N:14][N:18]=3)[C:20]2=[O:48])[CH:38]=[CH:37][C:36]=1[Cl:39]

Participants

Conditions

Temperature: 100 °C

Procedure

Tributyltin azide (0.340 mL, 1.24 mmol) was added to a solution of tert-butyl (6R,7R)-6-[(3-cyano-2-oxopyridin-1(2H)-yl)methyl]-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (198 mg, 0.41 mmol) in toluene (5 mL). The reaction mixture was stirred at 100° C. overnight. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (148 mg, 0.284 mmol, 68.6%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-2f66562d7c9c4fc38245b0ccf073b01e
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722662B2

Reaction notes

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