Ethyl Acetate → N-(5-benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide

HRID 1846836Notes

Reaction equation

HRID 1846836 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:28])[CH:11]=[C:12]([CH2:17][NH:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])[O:13][C:14]=1[CH2:15][OH:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C>>[CH2:1]([O:8][C:9]1[C:10](=[O:28])[CH:11]=[C:12]([CH2:17][NH:18][S:19]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)(=[O:21])=[O:20])[O:13][C:14]=1[CH:15]=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 86725693N-(5-benzyloxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide

Product 1

HCID 86725694N-(5-benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamideYield 71.71%

Conditions

Temperature
60 °C

Procedure

To a stirred solution of N-(5-benzyloxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide (10-01) (2.8 g, 6.98 mmol) in ethyl acetate (100 mL) IBX (2-iodoxy benzoic acid) (5.86 gm, 20.95 mmol) was added and the reaction mixture was heated up to 60° C. for 6 h. After completion of the reaction, the reaction mixture was filtered and concentrated to get the crude compound. It was then purified using normal column chromatography to get N-(5-benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide (11-01) (2.0 g, 71.71%) as a gummy liquid.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated
  4. customto get the crude compound
  5. customIt was then purified

Sources & evidence

ORD record
ord-fc119301a2d64e688facee0f764d093a
Source dataset
uspto-grants-2015_02
Patent number
US08952039B2

Reaction notes

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