Tetrahydrofuran → HCID 86678221、化合物

反応式

[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[N:9]2[C:19](=[O:32])[N:20]([CH2:22][CH2:23][CH2:24][S:25]([CH2:28][CH2:29][CH2:30][OH:31])(=[O:27])=[O:26])[N:21]=[C:8]2[N:7]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[CH:34]=2)[C:6]=1[CH3:43])=[O:4].[H-].[Na+].[C:46]1(C)[C:47]([S:52](Cl)(=[O:54])=[O:53])=[CH:48][CH:49]=[CH:50][CH:51]=1.[CH2:57]1COCC1>>[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:12]=[CH:13][C:14]([C:17]#[N:18])=[CH:15][CH:16]=2)[N:9]2[C:19](=[O:32])[N:20]([CH2:22][CH2:23][CH2:24][S:25]([CH2:28][CH2:29][CH2:30][O:31][S:52]([C:47]3[CH:46]=[CH:51][C:50]([CH3:57])=[CH:49][CH:48]=3)(=[O:53])=[O:54])(=[O:26])=[O:27])[N:21]=[C:8]2[N:7]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:40])([F:42])[F:41])[CH:34]=2)[C:6]=1[CH3:43])=[O:4]

参加物

反応物 4

HCID 8028Tetrahydrofuran

HCID 8623o-Toluenesulfonyl chloride

HCID 24758Sodium hydride

HCID 71293490HCID 71293490、化合物

生成物 1

HCID 86678221HCID 86678221、化合物

実験手順

Intermediate 22 (89 mg, 0.14 mmol) was dissolved in THF (3 ml), and then sodium hydride (6 mg, 0.2 mmol) was added under an atmosphere of N2. The reaction mixture was stirred at RT for 10 mins, then toluenesulfonyl chloride (31 mg, 0.16 mmol) was added and stirring was continued for 16 hours. The reaction mixture was partitioned between EtOAc and water. The organic layer was separated, washed with brine, dried (Na2SO4) and evaporated in vacuo. The resulting residue was purified by silica gel chromatography eluding with a gradient of 50-80% EtOAc in cyclohexane to yield the title compound as a colourless oil (70 mg).