Potassium Carbonate → HCID 10194637, compound
Reaction equation
C([O-])([O-])=O.[K+].[K+].[OH:7][C@@H:8]([C@@:10]1([CH3:31])[C@H:14]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([OH:23])[CH:16]=2)[CH2:13][N:12]([C:24](=[O:30])[CH2:25][S:26][C:27](=[O:29])[CH3:28])[CH2:11]1)[CH3:9].[CH:32]1([CH2:35]Br)[CH2:34][CH2:33]1>CN(C=O)C.O>[OH:7][C@@H:8]([C@@:10]1([CH3:31])[C@H:14]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH2:35][CH:32]3[CH2:34][CH2:33]3)[CH:16]=2)[CH2:13][N:12]([C:24](=[O:30])[CH2:25][S:26][C:27](=[O:29])[CH3:28])[CH2:11]1)[CH3:9]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
To a flask containing anhydrous K2CO3 (52 mg, 0.37 mmol, 4.0 eq) under a nitrogen atmosphere was added a solution of Example 118 (34 mg, 0.093 mmol, 1 eq) in anhydrous DMF (1 mL). Cyclopropylmethyl bromide (40 μL, 0.37 mmol, 4.0 eq) was added via syringe to the mixture. The slurry was stirred at 65° C. overnight. The reaction was cooled to room temperature, then diluted with water (50 mL). The aqueous solution was extracted with EtOAc (3×30 mL), and the combined organic layers were washed with brine (50 mL), then dried over Na2SO4, filtered, and concentrated in vacuo. The resulting oil was purified by preparative TLC plate (100% EtOAc), yielding a clear, colorless oil (13.9 mg, 36%).
Workup
- temperatureThe reaction was cooled to room temperature
- extractionThe aqueous solution was extracted with EtOAc (3×30 mL)
- washthe combined organic layers were washed with brine (50 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe resulting oil was purified by preparative TLC plate (100% EtOAc)
Sources & evidence
- ORD record
- ord-31ab9879fa9842c4b5f14efb4d8380d2
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06716871B2
Reaction notes
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