Sodium hydride → HCID 21048980、化合物

反応式

[CH2:1]([O:3][C:4](=[O:36])[CH:5]([S:32]([CH3:35])(=[O:34])=[O:33])[CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][C:11]([S:22]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)(=[O:24])=[O:23])([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[F:21])[CH2:10][CH2:9]1)[CH3:2].[H-].[Na+].FC(F)(F)S(O[CH2:45][CH3:46])(=O)=O>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:36])[C:5]([CH2:45][CH3:46])([S:32]([CH3:35])(=[O:33])=[O:34])[CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][C:11]([S:22]([C:25]2[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=2)(=[O:24])=[O:23])([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[F:21])[CH2:12][CH2:13]1)[CH3:2]

参加物

実験手順

A solution of the product from Example 108 (620 mg, 1.10 mmol) in N,N-dimethylformamide (2.5 mL) was added dropwise to a solution of sodium hydride (60% dispersion in mineral oil, 48 mg, 1.21 mmol) in N,N-dimethylformamide (2.5 mL), and stirred for 45 minutes. Ethyl trifluoromethanesulfonate (0.140 mL, 1.10 mmol) was added dropwise and stirred for 14 hours at room temperature. The reaction was partitioned between diethyl ether (150 mL) and 1M aqueous hydrochloric acid (150 mL), the phases were separated and the aqueous layer extracted with diethyl ether. The combined organic layers were washed with 1N aqueous sodium hydrogencarbonate and brine, dried over MgSO4 and concentrated. The residue was chromatographed using a Biotage™ 40S column, eluting with 70/30 iso-hexane/acetone to give the title compound (80 mg).