CID 6327156 → HCID 131733867, compound
Reaction equation
C([C@H]1COC(=O)N1[C:14](=[O:33])[C@H:15]([C:25]1[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][C:26]=1[CH3:32])[CH2:16][O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)C1C=CC=CC=1.[Li].[Li+].[O-:36][O-]>C1COCC1.O>[CH2:18]([O:17][CH2:16][C@@H:15]([C:25]1[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][C:26]=1[CH3:32])[C:14]([OH:33])=[O:36])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 16D (11.2 g, 22.03 mmol) in THF (70 ml) and water (20 ml) at 0° C. was added a solution of lithium peroxide [prepared by adding hydrogen peroxide (11.25 ml, 110 mmol) to lithium hydroxide (1.387 g, 33.0 mmol) in water (20 ml)] dropwise. The mixture was stirred at 0° C. for 1 h, then quenched with sat. sodium sulfite, and organic solvent was removed under reduced pressure. The remaining solution was diluted by 50 ml of water and extracted with dichloromethane (2×20 ml). The aqueous layer was acidified using conc. HCl. The solution was then extracted with ethyl acetate (3×). The organic extracts was combined and washed with brine and dried over sodium sulfate. The solution was filtered, concentrated and dried in vacuo to give 16E (8 g, 22.91 mmol, 104% yield) as an oil. MS (ESI) (m/z): 347, 349.4 (M−H)+.
Workup
- customquenched with sat. sodium sulfite, and organic solvent
- customwas removed under reduced pressure
- additionThe remaining solution was diluted by 50 ml of water
- extractionextracted with dichloromethane (2×20 ml)
- extractionThe solution was then extracted with ethyl acetate (3×)
- washwashed with brine
- dry with materialdried over sodium sulfate
- filtrationThe solution was filtered
- concentrationconcentrated
- customdried in vacuo
Sources & evidence
- ORD record
- ord-300814fafbbb4dda86d54e0801f5fbd0
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174974B2
Reaction notes
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