Cornforth reagent → HCID 59722681, compound
Reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=1[C@H:30]1[CH2:36][NH:35]/[C:34](=[N:37]\[CH2:38][CH:39](O)[CH2:40][C:41]([F:44])([F:43])[F:42])/[C@H:33]([NH:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])[CH2:32][CH2:31]1>C(#N)C>[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=1[C@H:30]1[CH2:36][N:35]2[C:39]([CH2:40][C:41]([F:44])([F:43])[F:42])=[CH:38][N:37]=[C:34]2[C@H:33]([NH:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])[CH2:32][CH2:31]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Pyridinium dichromate (2.24 g, 5.94 mmol) was added to a solution of tert-butyl {(2Z,3R,6S)-6-(2,6-difluorophenyl)-2-[(4,4,4-trifluoro-2-hydroxybutyl)imino]azepan-3-yl}carbamate (461 mg, 0.99 mmol) in acetonitrile (20 mL). After 18 h, the mixture was filtered and concentrated. Saturated aqueous sodium bicarbonate was added and the mixture was extracted with dichloromethane (3×). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. Purification by silica gel chromatography (80% hexanes/ethyl acetate→50% hexanes/ethyl acetate) gave the title compound. MS 446.2 (M+1).