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

HRID 1846839Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1846839
[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

Komponenten

4

Edukt 2

HCID 1118Sulfuric AcidHCID 867256966-(Benzene sulfonyl amino-methyl)-3-benzyloxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid

Produkt 1

HCID 867256976-(Benzene sulfonyl amino-methyl)-3-hydroxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acidAusbeute 47,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. customAfter completion of the reaction, it
  2. concentrationwas concentrated
  3. customthe reaction mixture was quenched with ice and solid
  4. customwas precipitated
  5. customResulted solid
  6. filtrationwas filtered
  7. customdried
  8. customto get the crude product
  9. washIt was then washed with 20% methanol and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a9bcd51ba8924c7da5c4136e560e5a2e
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952039B2

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