N-acetyl-N'-tert-butyl-5-formyl-6-methoxy-biphenyl-3,3'-disulfonamide → HCID 86607737, compound

HRID 2069979Notes

Reaction equation

HRID 2069979 reaction equation
[C:1]([NH:4][S:5]([C:8]1[CH:9]=[C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([NH:27]C(C)(C)C)(=[O:26])=[O:25])[CH:19]=2)[C:11]([O:16]C)=[C:12]([CH:14]=[O:15])[CH:13]=1)(=[O:7])=[O:6])(=[O:3])[CH3:2]>ClCCl>[C:1]([NH:4][S:5]([C:8]1[CH:9]=[C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([NH2:27])(=[O:26])=[O:25])[CH:19]=2)[C:11]([OH:16])=[C:12]([CH:14]=[O:15])[CH:13]=1)(=[O:7])=[O:6])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 86607706N-acetyl-N'-tert-butyl-5-formyl-6-methoxy-biphenyl-3,3'-disulfonamide

Product 1

HCID 86607737HCID 86607737, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-acetyl-N′-tert-butyl-5-formyl-6-methoxy-biphenyl-3,3′-disulfonamide (100 mg, 0.21 mmol), prepared as in Reference 19, was dissolved in dichloromethane (10 mL). The solution was flushed with nitrogen for 5 minutes and then boron tribromide (1.0 mL, 1M solution in dichloromethane) was added. The mixture was stirred at room temperature for 1 hour and then concentrated under by evaporation under reduced pressure. The residue was partitioned between water and ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The residue was passed through a short silica plug with pure ethyl acetate to give N-acetyl 5-formyl-6-hydroxy-biphenyl-3,3′-disulfonamide (74 mg) as a colorless oil.

Workup

  1. customThe solution was flushed with nitrogen for 5 minutes
  2. additionboron tribromide (1.0 mL, 1M solution in dichloromethane) was added
  3. concentrationconcentrated under by evaporation under reduced pressure
  4. customThe residue was partitioned between water and ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-140a0da882bf44e7be3f365ecc8490c0
Source dataset
uspto-grants-2012_10
Patent number
US08299110B2

Reaction notes

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