Sodium hydroxide tetrahydrofuran → 2-[3-Isopropyloxy-5-(2-fluorophenysulfonylmethyl)benzoylamino]-5-pridine carboxlic acid
Reaction equation
[OH-].[Na+].C1COCC1.[CH:8]([O:11][C:12]1[CH:13]=[C:14]([CH:28]=[C:29]([CH2:31][S:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[F:41])(=[O:34])=[O:33])[CH:30]=1)[C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([O:26]C)=[O:25])=[CH:20][N:19]=1)=[O:16])([CH3:10])[CH3:9]>>[CH:8]([O:11][C:12]1[CH:13]=[C:14]([CH:28]=[C:29]([CH2:31][S:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[F:41])(=[O:33])=[O:34])[CH:30]=1)[C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([OH:26])=[O:25])=[CH:20][N:19]=1)=[O:16])([CH3:10])[CH3:9]Participants
3
Procedure
Standard ester hydrolysis (2M NaOH/THF), as described in Example A, of methyl 2-[3-isopropyloxy-5-(2-fluorophenylsulfonyl) methyl benzoyl]aminopyridine-5-carboxylate gave the title compound as a pale yellow solid, 1H NMR δ (300 MHz, d6-DMSO): 1.12 (d, 6H); 4.58–4.66 (m, 1H); 4.79 (s, 2H); 6.98 (s, 1H); 7.30–7.41 (m, 2H); 7.43 (s, 1H); 7.48–7.63 (m, 2H); 7.72–7.81 (m, 1H); 8.30 (s, 2H); 8.86 (S, 1H); 11.08 (br s, 1H); m/z 473 (M+H)+, 471
Sources & evidence
- ORD record
- ord-ff12a680ab934b739f290705df853b87
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07160906B2
Reaction notes
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