Hydrochloric Acid → HCID 59180386, compound
Reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]([C:18]2[CH:22]=[CH:21][S:20][C:19]=2[C:23]([O:25][CH3:26])=[O:24])COC)(=[O:13])=[O:12])=[C:7]([C:27]#[N:28])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl>O1CCCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:18]2[CH:22]=[CH:21][S:20][C:19]=2[C:23]([O:25][CH3:26])=[O:24])(=[O:13])=[O:12])=[C:7]([C:27]#[N:28])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
To a solution of 37 (340.0 mg; 0.80 mmol) in tetrahydrofuran (16 mL) was added aqueous hydrochloric acid (5 mL; 10 mmol; 2N). The reaction mixture was heated at 75° C. for 4 hours, and then additional aqueous hydrochloric acid (3.0 mL; 6N) was added and the reaction mixture further heated at reflux for 4-5 hours. The reaction mixture was allowed to cool to room temperature and then extracted with ethyl acetate (15 mL). The organic layer was separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield an off-white residue which was triturated from diisopropyl ether to yield the title product as a white solid (240 mg).
Workup
- temperaturethe reaction mixture further heated
- temperatureat reflux for 4-5 hours
- temperatureto cool to room temperature
- extractionextracted with ethyl acetate (15 mL)
- customThe organic layer was separated
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customto yield an off-white residue which
- customwas triturated from diisopropyl ether
Sources & evidence
- ORD record
- ord-72edca6a320a485cad979328858108dd
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08178699B2
Reaction notes
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