Sodium Iodide → HCID 66976862, compound

HRID 1022796Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@@H:15]([CH2:16]I)[O:14][CH2:13][CH2:12][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[NH:33]1[CH2:38][CH2:37][CH:36]([C:39]([O:41][CH3:42])=[O:40])[CH2:35][CH2:34]1>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@@H:15]([CH2:16][N:33]3[CH2:38][CH2:37][CH:36]([C:39]([O:41][CH3:42])=[O:40])[CH2:35][CH2:34]3)[O:14][CH2:13][CH2:12][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of tert-butyl (6R,7S)-6-(3,4-dichlorophenyl)-7-(iodomethyl)-1,4-oxazepane-4-carboxylate (200 mg) in DMF (5 mL) were added potassium carbonate (170 mg), sodium iodide (190 mg) and methyl piperidine-4-carboxylate (88 mg), and the mixture was stirred at 100° C. overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (110 mg).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-363b3f672e6a4bc495e2a40e820decb6
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722662B2

Reaction notes

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