Hydrochloric Acid → 5-Bromo-6-methoxy-pyridine-3-sulfonic acid (2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-amide

HRID 268940

Reaction equation

HRID 268940 reaction equation
[OH:1][CH2:2][C:3]([NH:7][S:8]([C:11]1[CH:12]=[N:13][C:14](Cl)=[C:15]([Br:17])[CH:16]=1)(=[O:10])=[O:9])([CH2:5][OH:6])[CH3:4].[CH3:19][O-:20].[Na+].Cl>CO>[OH:1][CH2:2][C:3]([NH:7][S:8]([C:11]1[CH:12]=[N:13][C:14]([O:20][CH3:19])=[C:15]([Br:17])[CH:16]=1)(=[O:10])=[O:9])([CH2:5][OH:6])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 866079925-Bromo-6-chloro-N-(1,3-dihydroxy-2-methylpropan-2-yl)pyridine-3-sulfonamide

Product 1

HCID 670000755-Bromo-6-methoxy-pyridine-3-sulfonic acid (2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-amideYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-Bromo-6-chloro-pyridine-3-sulfonic acid (2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-amide (550 mg, 2 mmol) in MeOH (5 mL) was added a solution of sodium methoxide (c=5.4 mol/L in MeOH, 10 mmol) at rt for 48 h. The reaction mixture was poured into a 1N solution of HCl and was extracted with 2 portions of EtOAc, dried over Na2SO4, filtered, concentrated, and purified by column chromatography (heptane/EtOAc, 1:1) to give the title compound (0.28 g, 51%) as a white solid. MS (ISN) 353.1 [(M−H)−], 355.1 [(M+2−H)−].

Workup

  1. extractionwas extracted with 2 portions of EtOAc
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by column chromatography (heptane/EtOAc, 1:1)

Sources & evidence

ORD record
ord-30860c4336d840f880a82da224816964
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Linked notes

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