Hydrochloric Acid → Benzoic acid,3-chloro-5-[2-[[(1,1-dimethylethoxy)carbonyl]-4-pyridinylamino]ethoxy]-
Reaction equation
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([O:11][CH2:12][CH2:13][N:14]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[CH:5]=1.[OH-].[Na+].Cl>O1CCOCC1.O>[C:24]([O:23][C:21]([N:14]([C:15]1[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=1)[CH2:13][CH2:12][O:11][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([Cl:10])[CH:7]=1)[C:3]([OH:28])=[O:2])=[O:22])([CH3:27])([CH3:25])[CH3:26]Participants
6
Procedure
To a stirred solution of 3-[2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoic acid methyl ester (0.58 g) in a mixture of 1,4-dioxane (5 ml) and water (5 ml) was added 2M sodium hydroxide solution (0.72 ml). The reaction mixture was stirred at room temperature for 20 h, acidified by the addition of 2M hydrochloric acid (0.75 ml) and then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water, the aqueous layer removed and the organic phase washed with further water and dried with brine and over sodium sulphate. Concentration of the organic phase under reduced pressure gave the title compound as a yellow solid (0.32 g).
Workup
- concentrationconcentrated under reduced pressure
- customThe residue was partitioned between ethyl acetate and water
- customthe aqueous layer removed
- washthe organic phase washed with further water
- dry with materialdried with brine and over sodium sulphate
Sources & evidence
- ORD record
- ord-600ba2b5221442349b3609cb70cd1ff3
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06326386B1
Reaction notes
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