Water → HCID 86649161, compound

HRID 1925505Notes

Reaction equation

FC(F)(F)S([O:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)(=O)=O.O[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[C:8]12([CH2:7][O:6][C:21]3[CH:22]=[CH:23][C:24]([CH2:27][CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[CH:25][CH:26]=3)[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of Intermediate 34 (4.2 g, 14.07 mmol) in anhydrous dimethylformamide (12 mL) and a solution of Intermediate 20 (0.98 g, 4.14 mmol) in anhydrous dimethylformamide (2 mL) was added cesium carbonate (1.8 g, 5.62 mmol). The reaction mixture was stirred at 65° C. for 72 hours. The crude was poured into water and extracted with ether. The organic layer was washed with a solution of sodium hydroxide 2N, water and brine. The solvent was removed under reduced pressure and the title compound was obtained as an oil (1.3 g, 67%) and used in the next step without further purification. MS (M+): 386.

Workup

extractionextracted with ether
washThe organic layer was washed with a solution of sodium hydroxide 2N, water and brine
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-37f758099d3a46dfba0706b64c294e97
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178679B2

Reaction notes

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