Sodium Hydroxide → 6-Chloro-7-(4-(8-methylquinolin-2-ylcarbamoyl)phenoxy)chroman-4-carboxylic acid
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:32])[NH:20][C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[C:24]([CH3:31])[CH:25]=[CH:26][CH:27]=4)[N:22]=3)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:33]([O:35]CC)=[O:34].[OH-].[Na+]>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19](=[O:32])[NH:20][C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[C:24]([CH3:31])[CH:25]=[CH:26][CH:27]=4)[N:22]=3)=[CH:17][CH:18]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:33]([OH:35])=[O:34]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of ethyl 6-chloro-7-(4-(8-methylquinolin-2-ylcarbamoyl)phenoxy)chroman-4-carboxylate (0.024 g, 0.0464 mmol) in 3:1 THF/MeOH (1 ml) was added 1M sodium hydroxide (0.0511 ml, 0.0511 mmol), and the reaction was stirred for 16 hours at ambient temperature. The reaction was concentrated to dryness and acidified with diluted hydrochloric acid. The reaction was extracted with EtOAc twice, and the combined organics were dried over anhydrous sodium sulfate, filtered, and concentrated to yield the desired compound (0.02 g, 0.0409 mmol, 88.1% yield). MS (apci) m/z=489.1 (M+H).
Workup
- concentrationThe reaction was concentrated to dryness
- extractionThe reaction was extracted with EtOAc twice
- dry with materialthe combined organics were dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-5a2ad45c67a645f298f4c9ef73f6ef49
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785445B2
Reaction notes
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