6-(Benzene sulfonyl amino-methyl)-3-hydroxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid → 6-[(4-Chloro-benzenesulfonylamino)-methyl]-3-hydroxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid

HRID 1846887Notes

Reaction equation

HRID 1846887 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[CH:13]=[C:12]([CH2:16][NH:17][S:18]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[N:11]([CH3:28])[C:10]=1[C:29]([OH:31])=[O:30])C1C=CC=CC=1.C1(S(C(N)C2N(C)C(C(O)=O)=C(O)C(=O)C=2)(=O)=O)C=CC=CC=1>>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([S:18]([NH:17][CH2:16][C:12]2[N:11]([CH3:28])[C:10]([C:29]([OH:31])=[O:30])=[C:9]([OH:8])[C:14](=[O:15])[CH:13]=2)(=[O:19])=[O:20])=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 867256976-(Benzene sulfonyl amino-methyl)-3-hydroxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acidHCID 867257433-Benzyloxy-6-[(4-chloro-benzenesulfonylamino)-methyl]-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid

Product 1

HCID 867257446-[(4-Chloro-benzenesulfonylamino)-methyl]-3-hydroxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acidYield 31.6%

Procedure

6-[(4-Chloro-benzenesulfonylamino)-methyl]-3-hydroxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid (14-07) (140.0 mg, 31.55%) was synthesized as a brown solid from 3-benzyloxy-6-[(4-chloro-benzenesulfonylamino)-methyl]-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid (13-07) (550.0 mg, 1.19 mmol) following the procedure described for 6-(benzenesulfonylamino-methyl)-3-hydroxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid (14-01).

Sources & evidence

ORD record
ord-474b44b1e580440c8db3f9033312218d
Source dataset
uspto-grants-2015_02
Patent number
US08952039B2

Reaction notes

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