Water → HCID 178522996, compound

HRID 920682Notes

Reaction equation

HRID 920682 reaction equation
Cl([O-])=O.[Na+].S(=O)(=O)(O)N.[CH2:10]([O:17][C:18]1[C:19]([CH:36]=[O:37])=[N:20][CH:21]=[C:22]([C:34]=1[OH:35])[C:23]([NH:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)=[O:24])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH2:38]>O1CCCC1>[CH2:10]([O:17][C:18]1[C:19]([C:36]([OH:38])=[O:37])=[N:20][CH:21]=[C:22]([C:23](=[O:24])[NH:25][CH2:26][C:27]2[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=2)[C:34]=1[OH:35])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5987Sulfamic AcidHCID 23668197Sodium ChloriteHCID 1785199845-benzyloxy-N-(4-fluoro-benzyl)-6-formyl-4-hydroxy-nicotinic acid amide

Product 1

HCID 178522996HCID 178522996, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an aqueous solution (10 ml) of sodium chlorite (7.13 g, 78.8 mmol), and sulfamic acid (7.65 g, 78.8 mmol) was added a solution of the compound 12 (15.0 g, 39.4 mmol) in tetrahydrofuran (630 ml) under ice-cooling, and the mixture was stirred at room temperature for 1 hour. After water (250 ml) was added to the reaction solution, precipitated crystals were filtered. Washing with diethyl ether afforded 3-benzyloxy-5-(4-fluoro-benzylcarbamoyl)-4-hydroxy-pyridine-2-carboxylic acid 13 (14.0 g, 90%) as a colorless crystal.

Workup

  1. temperaturecooling
  2. customprecipitated crystals
  3. filtrationwere filtered
  4. washWashing with diethyl ether

Sources & evidence

ORD record
ord-562437a32dea4a3aa8f7e75c846cddab
Source dataset
uspto-grants-2016_03
Patent number
US09273065B2

Reaction notes

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