Potassium Hydroxide → 1-(Tert-butoxycarbonyl)-4-butyl-1,2,3,4-tetrahydroquinoxaline-6-carboxylic acid
Reaction equation
[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17]C)=[O:16])[CH:13]=2)[N:8]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[OH-].[K+]>CO>[C:22]([O:21][C:19]([N:8]1[C:9]2[C:14](=[CH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11][CH:10]=2)[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:6][CH2:7]1)=[O:20])([CH3:25])([CH3:24])[CH3:23]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
To a stirred solution of 1-tert-butyl 6-methyl 4-butyl-3,4-dihydroquinoxaline-1,6(2H)-dicarboxylate (158 mg) in methanol (1.4 mL) was added 1 M potassium hydroxide (1.4 mL). The mixture was stirred at 40° C. for 12 h and then concentrated under reduced pressure. The residue was diluted with water and washed with ethyl acetate. The aqueous layer was acidified to pH 4 with 1 N hydrochloric acid and extracted with chloroform (4×100 mL). The combined organic extracts were dried (sodium sulfate), filtered, and concentrated under reduced pressure to give 120 mg of the title compound: 1H NMR (300 MHz, CDCl3) δ 7.55, 7.40, 7.37, 3.79, 3.38, 3.34, 1.60, 1.53, 1.39, 0.97.
Workup
- concentrationconcentrated under reduced pressure
- additionThe residue was diluted with water
- washwashed with ethyl acetate
- extractionextracted with chloroform (4×100 mL)
- dry with materialThe combined organic extracts were dried (sodium sulfate)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-75f8f798d30a46289e6d4bb1aa139bb3
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07176242B2
Reaction notes
Loading…