Potassium Carbonate → HCID 57692815, compound
Reaction equation
P(CCCC)(CCCC)CCCC.Br[C:15]1[S:16][CH:17]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:19]=1.C([O-])([O-])=O.[K+].[K+].C(=O)([S:33][CH2:34][CH2:35][C@H:36]1[C@@H:40]([O:41][S:42]([CH3:45])(=[O:44])=[O:43])[CH2:39][C@@H:38]([O:46][CH:47]2[CH2:52][CH2:51][CH2:50][CH2:49][O:48]2)[C@@H:37]1[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60])C>C(O)C.O>[CH3:45][S:42]([O:41][C@@H:40]1[C@H:36]([CH2:35][CH2:34][S:33][C:15]2[S:16][CH:17]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:19]=2)[C@@H:37]([CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60])[C@H:38]([O:46][CH:47]2[CH2:52][CH2:51][CH2:50][CH2:49][O:48]2)[CH2:39]1)(=[O:43])=[O:44]Participants
7
Conditions
- Temperature
- 40 °C
Procedure
PBu3 (20 μL, 0.08 mmol), ethyl 2-bromothiazole-4-carboxylate (6-5, 119 mg, 0.50 mmol) and K2CO3 (107 mg, 0.77 mmol) were added to a solution of 6-3 (183 mg, 0.38 mmol) in 1.6 mL ethanol. The mixture was stirred at 40° C. overnight and then 20 mL H2O was added. The resulting mixture was extracted with ethyl acetate (30 mL) and the ethyl acetate solution was washed with brine (20 mL). The solution was then dried (Na2SO4), filtered, and evaporated. Purification of the residue by flash chromatography on silica gel (Combiflash unit by Isco) gave the title compound (41 mg, 18%).
Workup
- extractionThe resulting mixture was extracted with ethyl acetate (30 mL)
- washthe ethyl acetate solution was washed with brine (20 mL)
- dry with materialThe solution was then dried (Na2SO4)
- filtrationfiltered
- customevaporated
- customPurification of the residue by flash chromatography on silica gel (Combiflash unit by Isco)
Sources & evidence
- ORD record
- ord-efc2114d055b4306a6f8c570626e8f5f
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09006464B2
Reaction notes
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