Lithium Hydroxide → {[2-(6-Butoxy-pyridin-3-yl)-7-hydroxy-thiazolo[4,5-c]pyridine-6-carbonyl]-amino}-acetic acid
Reaction equation
C[O:2][C:3](=[O:29])[CH2:4][NH:5][C:6]([C:8]1[N:13]=[CH:12][C:11]2[N:14]=[C:15]([C:17]3[CH:18]=[N:19][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:21][CH:22]=3)[S:16][C:10]=2[C:9]=1[OH:28])=[O:7].[OH-].[Li+]>CO>[CH2:24]([O:23][C:20]1[N:19]=[CH:18][C:17]([C:15]2[S:16][C:10]3[C:9]([OH:28])=[C:8]([C:6]([NH:5][CH2:4][C:3]([OH:29])=[O:2])=[O:7])[N:13]=[CH:12][C:11]=3[N:14]=2)=[CH:22][CH:21]=1)[CH2:25][CH2:26][CH3:27]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of {[2-(6-butoxy-pyridin-3-yl)-7-hydroxy-thiazolo[4,5-c]pyridine-6-carbonyl]-amino}-acetic acid methyl ester (10.6 mg, 0.026 mmol) in methanol (1 mL) was added lithium hydroxide aqueous solution (1N, 0.51 mL) at ambient temperature. The reaction mixture was stirred at 50° C. for 1.5 h. After the solvent was evaporated off, 10 mL of water was added. The aqueous solution was adjusted to pH 2-3 by addition of 1N hydrochloric acid, and extracted twice with ethyl acetate. The combined organic layers were dried, filtered, and concentrated to afford 6.5 mg of a white solid. MS: (+) m/z 403.3 (M+1).
Workup
- customAfter the solvent was evaporated off
- addition10 mL of water was added
- additionThe aqueous solution was adjusted to pH 2-3 by addition of 1N hydrochloric acid
- extractionextracted twice with ethyl acetate
- customThe combined organic layers were dried
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-2a5d97710b68464d872fb1f490e5b8f8
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07696223B2
Reaction notes
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