N-acetyl-N-tert-butyl-5-formyl-6-methoxy-biphenyl-3,3'-disulfonamide → N-acetyl 5-formyl-6-hydroxy-biphenyl-3,3'-disulfonamide

HRID 1752931ノート

反応式

HRID 1752931 の反応式
[C:1]([N:4](C(C)(C)C)[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]([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]

参加物

3

反応物 1

HCID 86687864N-acetyl-N-tert-butyl-5-formyl-6-methoxy-biphenyl-3,3'-disulfonamide

生成物 1

HCID 86607737N-acetyl 5-formyl-6-hydroxy-biphenyl-3,3'-disulfonamide収率 88.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-31cbe35b3f4f4256bd35189563a44562
出典データセット
uspto-grants-2015_10
特許番号
US09162986B2

反応ノート

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