Hydrochloric Acid → 4-[2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-7-methyl-quinoline-2-carboxylic acid
Reaction equation
C([O:3][C:4]([C:6]1[CH:15]=[C:14]([O:16][CH2:17][C:18]([N:20]2[CH2:24][CH2:23][CH2:22][C@H:21]2[C:25](=[O:31])[NH:26][CH:27]2[CH2:30][CH2:29][CH2:28]2)=[O:19])[C:13]2[C:8](=[CH:9][C:10]([CH3:32])=[CH:11][CH:12]=2)[N:7]=1)=[O:5])C.[OH-].[Na+].Cl>C1COCC1>[CH:27]1([NH:26][C:25]([C@@H:21]2[CH2:22][CH2:23][CH2:24][N:20]2[C:18](=[O:19])[CH2:17][O:16][C:14]2[C:13]3[C:8](=[CH:9][C:10]([CH3:32])=[CH:11][CH:12]=3)[N:7]=[C:6]([C:4]([OH:5])=[O:3])[CH:15]=2)=[O:31])[CH2:28][CH2:29][CH2:30]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2.5 g 4-[2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-7-methyl-quinoline-2-carboxylic acid ethyl ester in 20 ml of THF, 5.7 ml of a 1M aqueous sodium hydroxide solution was added and stirred for 16 h at RT. The reaction mixture was acidified with 1M hydrochloric acid to pH 3 and the solvents were evaporated under reduced pressure. The residue was dissolved in a mixture of methanol/DCM and the solids were filtered off. The filtrate was evaporated under reduced pressure to yield the product which was pure enough for the next reaction step. Yield: 2.0 g.
Workup
- customthe solvents were evaporated under reduced pressure
- dissolutionThe residue was dissolved in a mixture of methanol/DCM
- filtrationthe solids were filtered off
- customThe filtrate was evaporated under reduced pressure
- customto yield the product which
- customwas pure enough for the next reaction step
Sources & evidence
- ORD record
- ord-77bb193fd4194e95b357ff74015e98b5
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08669266B2
Reaction notes
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