Triethylamine → 4-{[4-(Methylthio)-1,3-thiazol-2-yl]carbamoyl}phenyl acetate
Reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](Cl)=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.[CH3:21][S:22][C:23]1[N:24]=[C:25]([NH2:28])[S:26][CH:27]=1>C1COCC1>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:12])[NH:28][C:25]2[S:26][CH:27]=[C:23]([S:22][CH3:21])[N:24]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]Participants
Procedure
Into a solution of 510 (0.815 g, 4.10 mmol) and dry THF (20.0 mL) was added a solution of triethylamine (0.572 mL, 4.10 mmol) and dry THF (5.00 mL), followed by a solution of 508 (0.500 g, 3.42 mmol) dissolved in dry THF (15.0 mL). The reaction was stirred at room temperature. After stirring overnight, the reaction was concentrated in vacuo. The residue was partitioned between a saturated aqueous sodium bicarbonate and dichloromethane. The dichloromethane layer was washed a second time with the saturated sodium bicarbonate solution and than twice with aq. 1 M HCl. The dichloromethane layer was dried over anhydrous magnesium sulfate and concentrated in vacuo to give crude 512 (1.15 g, >100%) as a brown solid. The crude product was suspended in diethyl ether, stirred and filtered. The filter pad was washed with ether several times, and dried in vacuo to give 512 (0.692 g, 63%) as a light brown solid.
Workup
- stirringAfter stirring overnight
- concentrationthe reaction was concentrated in vacuo
- customThe residue was partitioned between a saturated aqueous sodium bicarbonate and dichloromethane
- washThe dichloromethane layer was washed a second time with the saturated sodium bicarbonate solution
- dry with materialThe dichloromethane layer was dried over anhydrous magnesium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-e4ca9d8793a043328e2c61be81ef0ad3
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772502B2
Reaction notes
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