Methanol → HCID 16074587, compound
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:16]=[CH:15][S:14][C:13]=2[C:17]([O:19]C)=[O:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+].CO>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][C:12]2[CH:16]=[CH:15][S:14][C:13]=2[C:17]([OH:19])=[O:18])(=[O:9])=[O:10])=[CH:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
To a solution of 74 (0.20 g; 5.32 mmol) in tetrahydrofuran (2.7 mL) were added aqueous sodium hydroxide (2.7 mL; 2N) and methanol (1.4 mL), sequentially. The reaction mixture was heated at 65° C. for 18 hours, allowed to cool to room temperature, and then extracted with aqueous sodium hydroxide (20 mL; 2N). The aqueous layer was washed with diethyl ether (30 mL×2), acidified with aqueous hydrochloric acid (20 mL; 6N), and extracted with dichloromethane (40 mL). The organic layer was successively washed with water (30 mL) and aqueous saturated sodium chloride (30 mL), dried over magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to yield the title compound as a white solid (0.18 g).
Workup
- temperatureto cool to room temperature
- extractionextracted with aqueous sodium hydroxide (20 mL; 2N)
- washThe aqueous layer was washed with diethyl ether (30 mL×2)
- extractionextracted with dichloromethane (40 mL)
- washThe organic layer was successively washed with water (30 mL) and aqueous saturated sodium chloride (30 mL)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-e7d8a948f2ae41989f273e97cd4369a1
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08178699B2
Reaction notes
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