Potassium Carbonate → HCID 54530255, Verbindung

HRID 24656

Reaktionsgleichung

Reaktionsgleichung von HRID 24656
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH2:4]Cl.[CH3:11][O:12][C:13](=[O:32])[C@H:14]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([OH:31])[CH:25]=1)[NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C([O-])([O-])=O.[K+].[K+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CN(C=O)C.O>[CH3:11][O:12][C:13](=[O:32])[C@H:14]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:4][C:3]2[C:2]([Cl:1])=[CH:9][CH:8]=[CH:7][C:6]=2[Cl:10])=[C:26]([O:31][CH2:4][C:3]2[C:2]([Cl:1])=[CH:9][CH:8]=[CH:7][C:6]=2[Cl:10])[CH:25]=1)[NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 748322,6-Dichlorobenzyl chlorideHCID 14889488(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(3,4-dihydroxyphenyl)propanoate

Produkt 1

HCID 54530255HCID 54530255, VerbindungAusbeute 71,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2,6-Dichlorobenzyl chloride (1.73 g) was added to a suspension of N-(tert-butoxycarbonyl)-3,4-dihydroxy-L-phenylalanine methyl ester (2.5 g), K2CO3 (2.22 g), and n-Bu4NI (0.297 g) in DMF (15 mL) at room temperature. The mixture was stirred overnight at room temperature, diluted with water and extracted with ether. The extract was dried (MgSO4) and evaporated. The residue was purified by column chromatography (silica gel; eluent: hexanes/CH2Cl2/EtOAc, 5:5:1) to yield N-(tert-butoxycarbonyl)-3,4-bis(2,6-dichlorobenzyloxy)-L-phenylalanine methyl ester (2.0 g), ESMS: m/z 630 (MH+), N-(tert-butoxycarbonyl)-3-(2,6-dichlorobenzyloxy)-4-hydroxy-L-phenylalanine methyl ester (0.39 g), ESMS: m/z 470(MH+), and N-(tert-butoxycarbonyl)-4-(2,6-dichlorobenzyloxy)-3-hydroxy-L-phenylalanine methyl ester (0.45 g), ESMS: m/z 470 (MH+), respectively.

Aufarbeitung

  1. extractionextracted with ether
  2. dry with materialThe extract was dried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by column chromatography (silica gel; eluent: hexanes/CH2Cl2/EtOAc, 5:5:1)

Quellen und Nachweise

ORD-Eintrag
ord-8e727efff0af4a0187c6413082883345
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855843B2

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