Sulfuric Acid → 6-(Benzene sulfonyl amino-methyl)-3-hydroxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid

HRID 1846839Notes

Reaction equation

[C:1]1([S:7]([CH:10]([NH2:30])[C:11]2[N:16]([CH3:17])[C:15]([C:18]([OH:20])=[O:19])=[C:14]([O:21]CC3C=CC=CC=3)[C:13](=[O:29])[CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O>C(O)(=O)C>[C:1]1([S:7]([CH:10]([NH2:30])[C:11]2[N:16]([CH3:17])[C:15]([C:18]([OH:20])=[O:19])=[C:14]([OH:21])[C:13](=[O:29])[CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 6-(benzene sulfonyl amino-methyl)-3-benzyloxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid (13-01) (430.0 mg, 1.005 mmol) in acetic acid (15 mL) was added sulfuric acid (0.011 mL) and the reaction mixture was heated at 80° C. for 24 h. After completion of the reaction, it was concentrated and the reaction mixture was quenched with ice and solid was precipitated. Resulted solid was filtered and dried to get the crude product. It was then washed with 20% methanol and ethyl acetate to get 6-(benzene sulfonyl amino-methyl)-3-hydroxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid (14-01) (160.0 mg, 47.07%) as an off white solid.

Workup

customAfter completion of the reaction, it
concentrationwas concentrated
customthe reaction mixture was quenched with ice and solid
customwas precipitated
customResulted solid
filtrationwas filtered
customdried
customto get the crude product
washIt was then washed with 20% methanol and ethyl acetate

Sources & evidence

ORD record: ord-a9bcd51ba8924c7da5c4136e560e5a2e
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952039B2

Reaction notes

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