Water → 6-(benzene sulfonyl amino-methyl)-3-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid

HRID 1846837Notes

Reaction equation

HRID 1846837 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:28])[CH:11]=[C:12]([CH2:17][NH:18]S(C2C=CC=CC=2)(=O)=O)[O:13][C:14]=1[CH:15]=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:29](=[O:33])(=O)([OH:31])N.Cl([O-])=O.[Na+].[OH2:38]>CC(C)=O>[C:2]1([S:29]([CH:17]([NH2:18])[C:12]2[O:13][C:14]([C:15]([OH:16])=[O:38])=[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:10](=[O:28])[CH:11]=2)(=[O:33])=[O:31])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5987Sulfamic AcidHCID 23668197Sodium ChloriteHCID 86725694N-(5-benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide

Product 1

HCID 867256956-(benzene sulfonyl amino-methyl)-3-benzyloxy-4-oxo-4H-pyran-2-carboxylic acidYield 87.82%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of N-(5-benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide (11-01) (700.0 mg, 1.75 mmol) in acetone (10 mL) and water (15 mL) were added sulfamic acid (240.45 mg, 2.45 mmol) and sodium chlorite (166.6 mg, 1.84 mmol) and the reaction mixture was allowed to stir for 16 h at room temperature. After completion of the reaction, the solvent and the volatile substances were removed and extracted with dichloromethane. The combined organic layer was washed with saturated ammonium chloride solution, water and then brine, dried over Na2SO4 and concentrated under reduced pressure to get 6-(benzene sulfonyl amino-methyl)-3-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid (12-01) (640.0 mg, 87.82%) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent and the volatile substances were removed
  3. extractionextracted with dichloromethane
  4. washThe combined organic layer was washed with saturated ammonium chloride solution, water
  5. dry with materialbrine, dried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aaa910c5384e44d2a9c78fafa9f052bb
Source dataset
uspto-grants-2015_02
Patent number
US08952039B2

Reaction notes

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