Iodine → HCID 86701056, compound
Reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.II.[CH2:22]([O:29][N:30]1[C:36](=[O:37])[N:35]2[CH2:38][C@H:31]1[CH2:32][CH2:33][C@H:34]2[C:39]([NH:41][NH:42][C:43]([C@H:45]1[CH2:49][CH2:48][C@@H:47]([NH:50][C:51](=[O:57])[O:52][C:53]([CH3:56])([CH3:55])[CH3:54])[CH2:46]1)=[O:44])=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH2:22]([O:29][N:30]1[C:36](=[O:37])[N:35]2[CH2:38][C@H:31]1[CH2:32][CH2:33][C@H:34]2[C:39]1[O:44][C:43]([C@H:45]2[CH2:49][CH2:48][C@@H:47]([NH:50][C:51](=[O:57])[O:52][C:53]([CH3:56])([CH3:54])[CH3:55])[CH2:46]2)=[N:42][N:41]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a 0° C. solution of PPh3 (2.2 g 8.4 mmol) in dry DCM (20 mL) was added I2 (2.1 g, 8.4 mmol). After I2 was dissolved, TEA (2.4 mL, 16.8 mmol) was added quickly at rt. The reaction mixture was stirred for 15 min. tert-Butyl (1R,3S)-3-(2-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)hydrazinecarbonyl)cyclopentylcarbamate (2.1 g, 4.2 mmol) was added. The reaction mixture was stirred at rt for 1 h. The reaction mixture was concentrated and the residue was purified by silica gel column (gradient elution 0-50% EtOAc/petroleum ether) to afford the crude tert-butyl (1R,3S)-3-(5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octan-2-yl)-1,3,4-oxadiazol-2-yl)cyclopentylcarbamate (−1.7 g) as a white solid. ESI-MS (EI+, m/z): 484.1.
Workup
- additionwas added
- concentrationThe reaction mixture was concentrated
- customthe residue was purified by silica gel column (gradient elution 0-50% EtOAc/petroleum ether)
Sources & evidence
- ORD record
- ord-c093073e12724789b19ac5d4bfdd422d
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933232B2
Reaction notes
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