Triethylamine → O-(2-diazo-1,3-dioxobutyl)-N-trifloroacetyl-L-serine
Reaktionsgleichung
[C:1]([O:7][CH2:8][C@@H:9]([C:17]([OH:19])=[O:18])[NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].C(N(CC)CC)C.C1(C)C=CC(S([N:36]=[N+:37]=[N-])(=O)=O)=CC=1>C(O)C>[N+:36](=[C:2]([C:3](=[O:4])[CH3:5])[C:1]([O:7][CH2:8][C@@H:9]([C:17]([OH:19])=[O:18])[NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])=[O:6])=[N-:37]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of O-acetoacetyl-N-trifluoroacetyl-L-serine (232 mg) and triethylamine (0.41 ml) in ethanol (7 ml) was added p-toluenesulfonyl azide (193 mg) at 0° C. The mixture was stirred for an hour at 0° C. and for 4 hours at room temperature. The solvent was distilled off in vacuo and the residue was diluted with chloroform and washed successively with aqueous acetic acid, water and brine. After drying over sodium sulfate, the chloroform extract was filtered and concentrated. The residue was flash chromatographed on silica gel (10 g) eluting successively with chloroform and a 1:9 mixture of methanol and chloroform to give O-(2-diazo-1,3-dioxobutyl)-N-trifloroacetyl-L-serine (193 mg).
Aufarbeitung
- distillationThe solvent was distilled off in vacuo
- additionthe residue was diluted with chloroform
- washwashed successively with aqueous acetic acid, water and brine
- dry with materialAfter drying over sodium sulfate
- extractionthe chloroform extract
- filtrationwas filtered
- concentrationconcentrated
- customchromatographed on silica gel (10 g)
- washeluting successively with chloroform
- additiona 1:9 mixture of methanol and chloroform
Quellen und Nachweise
- ORD-Eintrag
- ord-0f77168854cc4cc39edeae367afea197
- Quelldatensatz
- uspto-grants-1990_07
- Patentnummer
- US04939241
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