Boron tribromide → N-(2,6-dichlorobenzoyl)-4-(2-hydroxyphenyl)-L-phenylalanine methyl ester

HRID 1060414노트

반응식

HRID 1060414 반응식
B(Br)(Br)Br.[CH3:5][O:6][C:7](=[O:35])[C@H:8]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33]C)=[CH:23][CH:22]=1)[NH:9][C:10](=[O:19])[C:11]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:18]>C(Cl)Cl>[CH3:5][O:6][C:7](=[O:35])[C@H:8]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[OH:33])=[CH:23][CH:22]=1)[NH:9][C:10](=[O:19])[C:11]1[C:12]([Cl:18])=[CH:13][CH:14]=[CH:15][C:16]=1[Cl:17]

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 54267959N-(2,6-dichlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine methyl ester

생성물 1

HCID 54156646N-(2,6-dichlorobenzoyl)-4-(2-hydroxyphenyl)-L-phenylalanine methyl ester수율 50.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

BBr3 (1 mL, 1M in CH2Cl2) was added to a CH2Cl2 (10 mL) solution of N-(2,6-dichlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine methyl ester (0.215 g) at 0°0 C. with stirring and the solution was slowly warmed to room temperature. The mixture was stirred for 3 h and quenched with EtOH. The solvent was removed and the residue was taken up in EtOAc. The solution was washed with satd. NaHCO3 followed by brine, dried (MgSO4) and evaporated. The residue was purified by flash column chromatography (silica gel; eluent: hexanes/EtOAc 2:1) to yield 0.105 g of N-(2,6-dichlorobenzoyl)-4-(2-hydroxyphenyl)-L-phenylalanine methyl ester. ESMS: m/z 444 (MH+).

후처리

  1. stirringThe mixture was stirred for 3 h
  2. customquenched with EtOH
  3. customThe solvent was removed
  4. washThe solution was washed with satd
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by flash column chromatography (silica gel; eluent: hexanes/EtOAc 2:1)

출처 및 근거

ORD 기록
ord-cedb7585fe314b5892301083fc5273db
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06521666B1

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