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

HRID 1622159Notes

Reaction equation

HRID 1622159 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-68ed2e6906b0475797b1b7b88b7c15f3
Source dataset
uspto-grants-2014_07
Patent number
US08778625B2

Reaction notes

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