Sodium Hydroxide → 5-[((1-Decylsulfonyl)amino)carbonyl]-3-methoxypyridine-2-carboxylic acid

HRID 976027Notes

Reaction equation

HRID 976027 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([O:14][CH3:15])[C:7]([C:10]([O:12]C)=[O:11])=[N:8][CH:9]=1)([OH:3])=O.[CH2:16]([S:26]([NH2:29])(=[O:28])=[O:27])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].CC(C)([O-])C.[K+].N1C=CC=CC=1C(OC)=O.[OH-].[Na+]>>[CH2:16]([S:26]([NH:29][C:1]([C:4]1[CH:5]=[C:6]([O:14][CH3:15])[C:7]([C:10]([OH:12])=[O:11])=[N:8][CH:9]=1)=[O:3])(=[O:27])=[O:28])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 755692-CarbomethoxypyridineHCID 22923859Methyl 5-carboxy-3-methoxypyridine-2-carboxylateHCID 237214021-Decylsulfonamide potassium tert-butoxide

Product 1

HCID 199603575-[((1-Decylsulfonyl)amino)carbonyl]-3-methoxypyridine-2-carboxylic acid

Procedure

2.1 g (10 mmol) of methyl 5-carboxy-3-methoxypyridine-2-carboxylate (cf. Example 1d)) were reacted with N,N'-carbonyldiimidazole and 1-decylsulfonamide/potassium tert-butoxide in an analogous manner to that described in Example 1e) and the methyl pyridine-2-carboxylate thus obtained was hydrolyzed with 1N methanolic sodium hydroxide solution. After the aqueous solution had been acidified with cooling, 1.4 g of product were obtained, m.p. 145° C. (with dec.).

Workup

  1. customthus obtained
  2. temperaturewith cooling

Sources & evidence

ORD record
ord-940eeafc1112408dbea68cfe9684b243
Source dataset
uspto-grants-1997_03
Patent number
US05610172

Reaction notes

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