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

HRID 1752931노트

반응식

HRID 1752931 반응식
[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]

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-31cbe35b3f4f4256bd35189563a44562
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09162986B2

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