Water → Propane-1-sulfonic acid (4-fluoro-3 formyl phenyl)-amide

HRID 1965022Notes

Reaction equation

HRID 1965022 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH2:12][CH2:13][CH3:14])(=[O:11])=[O:10])=[CH:4][C:3]=1[CH2:15][OH:16].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.O>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH2:12][CH2:13][CH3:14])(=[O:11])=[O:10])=[CH:4][C:3]=1[CH:15]=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 58087735Propane-1 sulfonic acid (4 fluoro-3-hydroxymethyl-phenyl)-amide

Product 1

HCID 58086439Propane-1-sulfonic acid (4-fluoro-3 formyl phenyl)-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To propane-1-sulfonic acid (4-fluoro-3-hydroxymethyl-phenyl)-amide (671, 0.483 g, 0.00195 mol) in tetrahydrofuran (10.0 mL), cooled with ice/water, was added Dess-Martin periodinane (1.00 g, 0.00236 mol). The reaction was stirred at room temperature for 10 minutes. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 30% ethyl acetate in hexane to give a white solid (672, 360 mg, 75%). MS (ES1)[M−H+]−=244.1.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 30% ethyl acetate in hexane
  7. customto give a white solid (672, 360 mg, 75%)

Sources & evidence

ORD record
ord-95876b89dabf47879d374667aff3f8bf
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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