Methyl iodide → HCID 71110548, compound
Reaction equation
C(O[CH:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([O:19][C:20](=[O:22])[CH3:21])[C@H:7]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([CH2:30][C:31]3[CH:40]=[CH:39][C:34]4[O:35][CH2:36][CH2:37][O:38][C:33]=4[CH:32]=3)[CH:24]=2)[O:6]1)(=O)C.N[C:42](N)=[S:43].[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.CI.CCN(C(C)C)C(C)C>O1CCOCC1.CCOC(C)=O>[C:20]([O:19][C@@H:8]1[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:5]([S:43][CH3:42])[O:6][C@H:7]1[C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([CH2:30][C:31]2[CH:40]=[CH:39][C:34]3[O:35][CH2:36][CH2:37][O:38][C:33]=3[CH:32]=2)[CH:24]=1)(=[O:22])[CH3:21]Participants
8
Conditions
- Temperature
- 80 °C
Procedure
To a solution of compound 137 (200 mg, 0.35 mmol) and thiourea (53 mg, 0.70 mmol) in 1,4-dioxane (5.0 mL) was added TMSOTf (96 μL, 0.53 mmol) and the reaction mixture was heated to 80° C. for 3 h. The mixture was cooled to room temperature, and MeI (55 μL, 0.87 mmol) and DIPEA (0.30 mL, 1.75 mmol) were added thereto and the mixture was stirred for 3 h. The resulting mixture was diluted with EtOAc and washed with water. The organic layer was dried over dried over MgSO4, filtered, and concentrated in vacuo. The crude was purified by preparative HPLC (reverse phase) to provide the title compound (60 mg, 30%) as a white solid.
Workup
- temperatureThe mixture was cooled to room temperature
- washwashed with water
- customThe organic layer was dried
- dry with materialover dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude was purified by preparative HPLC (reverse phase)
Sources & evidence
- ORD record
- ord-b40e8b56026747238e0868ea00db811f
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09034921B2
Reaction notes
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