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

HRID 1060414Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1060414
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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 54156646N-(2,6-dichlorobenzoyl)-4-(2-hydroxyphenyl)-L-phenylalanine methyl esterAusbeute 50,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-cedb7585fe314b5892301083fc5273db
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521666B1

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