Sodium Hydroxide → 4-{2-[5-(2-Methoxy-phenyl)-pyridin-2-yloxy]-acetylamino}-thiophene-3-carboxylic acid
Reaction equation
C[O:2][C:3]([C:5]1[C:9]([NH:10][C:11](=[O:28])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[O:26][CH3:27])=[CH:16][N:15]=2)=[CH:8][S:7][CH:6]=1)=[O:4].[OH-].[Na+]>C(O)C>[CH3:27][O:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:17]1[CH:18]=[CH:19][C:14]([O:13][CH2:12][C:11]([NH:10][C:9]2[C:5]([C:3]([OH:4])=[O:2])=[CH:6][S:7][CH:8]=2)=[O:28])=[N:15][CH:16]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To 4-{2-[5-(2-methoxy-phenyl)-pyridin-2-yloxy]-acetylamino}-thiophene-3-carboxylic acid methyl ester (93 mg, 0.233 mmol) in ethanol (10 mL) was added a solution of sodium hydroxide (1N, 0.47 mL, 0.47 mmol) and the reaction was stirred at room temperature for 2 days. After such time the reaction mixture was filtered through glass wool and the filtrate was then neutralized by addition of a solution of hydrochloric acid (1N, 0.46 mL). Additional water was added to the solution (in excess of 10 mL) before the precipitate was isolated by filtration, washed with water and dried in vacuo to yield the title compound as a white solid (79 mg, 88%).
Workup
- filtrationAfter such time the reaction mixture was filtered through glass wool
- additionthe filtrate was then neutralized by addition of a solution of hydrochloric acid (1N, 0.46 mL)
- additionAdditional water was added to the solution (in excess of 10 mL) before the precipitate
- customwas isolated by filtration
- washwashed with water
- customdried in vacuo
Sources & evidence
- ORD record
- ord-24b71ded492e46158a383d3f9b9c939a
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07732452B2
Reaction notes
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