Potassium Carbonate → N-[2-[[(1,1-dimethylethoxy)carbonyl]-amino]-4-(methylthio)-1-oxobutyl]-beta-alanine, ethyl ester

HRID 378128

Reaktionsgleichung

Reaktionsgleichung von HRID 378128
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH2:11][S:12][CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:18]([O:20][C:21](=[O:25])[CH2:22][CH2:23][NH2:24])[CH3:19].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.N1C=CC=CC=1.CN(C1C=CN=CC=1)C.C([O-])(O)=O.[Na+]>[CH3:4][C:1]([CH3:2])([O:5][C:6]([NH:8][CH:9]([CH2:10][CH2:11][S:12][CH3:13])[C:14]([NH:24][CH2:23][CH2:22][C:21]([O:20][CH2:18][CH3:19])=[O:25])=[O:16])=[O:7])[CH3:3]

Komponenten

8

Edukt 3

HCID 11430Potassium CarbonateHCID 89857Boc-L-methionineHCID 458475beta-Alanine, ethyl ester, hydrochloride

Produkt 1

HCID 85152754N-[2-[[(1,1-dimethylethoxy)carbonyl]-amino]-4-(methylthio)-1-oxobutyl]-beta-alanine, ethyl esterAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A solution of N-(tert-butoxycarbonyl)-L-methionine (6.2 g) in DMF (25 ml) and pyridine (25 ml) was treated with DSC (9.6 g) and a catalytic amount of DMAP. After 4 hours, a solution of β-alanine ethyl ester HCl (3.8 g) and K2CO3 (3.5 g) in saturated aqueous NaHCO3 (25 ml) was added. The reaction mixture was stirred overnight at room temperature. The excess solvent was removed under reduced pressure and purified by HPLC (RP--CH3CN/H2O). N-[2-[[(1,1-dimethylethoxy)carbonyl]-amino]-4-(methylthio)-1-oxobutyl]-β-alanine, ethyl ester (7.0 g) as a colorless oil was obtained. The oil was confirmed as the desired product by MS and used without further purification.

Aufarbeitung

  1. customThe excess solvent was removed under reduced pressure
  2. custompurified by HPLC (RP--CH3CN/H2O)

Quellen und Nachweise

ORD-Eintrag
ord-432072e6407141fb8de154a6a1b3c967
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06028223

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