N-(2,6-Dichlorobenzoyl)-4-(4-allylamino-2,6-dimethoxyphenyl)-L-phenylalanine methyl ester → N-(2,6-dichlorobenzoyl)-4-(4-amino-2,6-dimethoxyphenyl)-L-phenylalanine methyl ester

HRID 1060436

Reaktionsgleichung

Reaktionsgleichung von HRID 1060436
[CH3:1][O:2][C:3](=[O:37])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:28]([O:29][CH3:30])=[CH:27][C:26]([NH:31]CC=C)=[CH:25][C:24]=2[O:35][CH3:36])=[CH:19][CH:18]=1)[NH:5][C:6](=[O:15])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14]>CC#N.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[CH3:1][O:2][C:3](=[O:37])[C@H:4]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[C:28]([O:29][CH3:30])=[CH:27][C:26]([NH2:31])=[CH:25][C:24]=2[O:35][CH3:36])=[CH:21][CH:22]=1)[NH:5][C:6](=[O:15])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14]

Komponenten

4

Edukt 1

HCID 53867698N-(2,6-Dichlorobenzoyl)-4-(4-allylamino-2,6-dimethoxyphenyl)-L-phenylalanine methyl ester

Produkt 1

HCID 54169167N-(2,6-dichlorobenzoyl)-4-(4-amino-2,6-dimethoxyphenyl)-L-phenylalanine methyl esterAusbeute 82,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)KatalysatorHCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Versuchsvorschrift

N-(2,6-Dichlorobenzoyl)-4-(4-allylamino-2,6-dimethoxyphenyl)-L-phenylalanine methyl ester (0.93 g) was dissolved in MeCN/water (40 mL of 84:16) under N2. Wilkinson's catalyst (79 mg ) was added and the mixture was brought to boiling. After 2 h, more catalyst (170 mg ) was added and the reaction continued for another 6 h. The solvent was evaporated and the residual water coevaporated with MeCN. The residue was purified by preparative TLC (silica gel; eluent: hexane/AcOEt 2:1 to 1:2) to give N-(2,6-dichlorobenzoyl)-4-(4-amino-2,6-dimethoxyphenyl)-L-phenylalanine methyl ester(708 mg).

Aufarbeitung

  1. waitthe reaction continued for another 6 h
  2. customThe solvent was evaporated
  3. customThe residue was purified by preparative TLC (silica gel; eluent: hexane/AcOEt 2:1 to 1:2)

Quellen und Nachweise

ORD-Eintrag
ord-6b0c7797476848c0b26d7fdfb9e9c5cb
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521666B1

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