p-Toluenesulfonic acid → HCID 2763195, compound
Reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:11][O:10][C:9]1=[O:12])(C)(C)C.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20]([OH:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.FC(F)(F)C(O)=O>>[O:12]=[C:9]1[C@@H:8]([NH3+:7])[CH2:11][O:10]1.[C:14]1([CH3:24])[CH:15]=[CH:16][C:17]([S:20]([O-:23])(=[O:21])=[O:22])=[CH:18][CH:19]=1Participants
5
Conditions
- Temperature
- 0 °C
Procedure
To a stirred mixture of 2 (1.34 mmol) and anhydrous p-toluenesulphonic acid (72 h under vacuum in the presence of P2O5) (1.43 mmol), kept at 0° C. under N2, trifluoroacetic acid (3 mL) was added dropwise in the course of 10 min. The solution was reacted under stirring at 0° C. for 15 min, allowed to reach room temperature, and concentrated at a temperature below 30° C. The oily residue was kept under vacuum for 1 h, and the resulting white solid triturated and washed with dry diethyl ether, then kept under vacuum for 24 h. Yield 81%. Mp and 1H NMR are in accordance with literature (Arnold, et al., 1988).
Workup
- customkept at 0° C. under N2
- customThe solution was reacted
- customto reach room temperature
- concentrationconcentrated at a temperature below 30° C
- waitThe oily residue was kept under vacuum for 1 h
- customthe resulting white solid triturated
- washwashed with dry diethyl ether
- waitkept under vacuum for 24 h
Sources & evidence
- ORD record
- ord-8a443917c8764817a3893f8fe4a38ce2
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321743B2
Reaction notes
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