Sodium hydroxide tetrahydrofuran → 2-[3-(2-Fluorobenzyloxy)-5-(5-methylisoxazol-3-ylmethoxymethyl)-benzoylamino]-5-pyridine carboxylic acid
Reaction equation
[OH-].[Na+].C1COCC1.[F:8][C:9]1[CH:44]=[CH:43][CH:42]=[CH:41][C:10]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:29]=[C:30]([CH2:32][O:33][CH2:34][C:35]2[CH:39]=[C:38]([CH3:40])[O:37][N:36]=2)[CH:31]=1)[C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([O:27]C)=[O:26])=[CH:21][N:20]=1)=[O:17]>>[F:8][C:9]1[CH:44]=[CH:43][CH:42]=[CH:41][C:10]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:29]=[C:30]([CH2:32][O:33][CH2:34][C:35]2[CH:39]=[C:38]([CH3:40])[O:37][N:36]=2)[CH:31]=1)[C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([OH:27])=[O:26])=[CH:21][N:20]=1)=[O:17]Participants
3
Reactant 2
Product 1
Procedure
Standard ester hydrolysis (2M NaOH/THF), as described in Example A, of methyl 2-[3-(2-fluorobenzyloxy)-5-(5-methyl isoxazol-3-yl methoxy) methyl benzoyl]aminopyridine-5-carboxylate gave the title compound as a colourless solid, 1H NMR δ (300 MHz, d6-DMSO): 2.40 (s, 3H); 4.58 (s, 4H), 5.22 (s, 2H); 6.26 (s, 1H); 7.21–7.30 (m, 3H); 7.38–7.45 (m, 1H); 7.55–7.60 (ap d, 1H); 7.60 (s, 1H); 7.64 (s, 1H); 8.32 (s, 2H); 8.86 (s, 1H); 11.16 (br s, 1H); m/z 492 (M+H)+, 490 (M−H)−
Sources & evidence
- ORD record
- ord-499c9885f48045eda5e813cfb012a495
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07160906B2
Reaction notes
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