Triethylamine → N-(1-adamantylcarbonyl)-L-alanyl-L-proline ethylamide

HRID 47049

Reaktionsgleichung

Br.[CH2:2]([NH:4][C:5](=[O:16])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:15])[C@H:12]([CH3:14])[NH2:13])[CH3:3].C(N(CC)CC)C.[C:24]12([C:34](Cl)=[O:35])[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[CH2:25]1)[CH2:31]2>O1CCCC1>[CH2:2]([NH:4][C:5](=[O:16])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:15])[C@H:12]([CH3:14])[NH:13][C:34]([C:24]12[CH2:33][CH:28]3[CH2:27][CH:26]([CH2:32][CH:30]([CH2:29]3)[CH2:31]1)[CH2:25]2)=[O:35])[CH3:3]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

2.93 g (0.010 mol) of L-alanyl-L-proline ethylamide hydrobromide were dissolved in 50 ml of tetrahydrofuran and the mixture was cooled to 0° C. There were then added 2.8 ml (0.020 mol) of triethylamine followed by 2.15 g (0.010 mol) of 1-adamantoyl chloride. The mixture was stirred at 0° C. for 0.5 hour and at room temperature for 2 hours and then evaporated to dryness. The oily residue was dissolved in ethyl acetate and the solution washed successively with 0.5-N hydrochloric acid, water, 5% sodium bicarbonate solution and water, dried over sodium sulphate and evaporated. The resulting oil was crystallised from ethyl acetate/petroleum ether to yield 2.2 g (59%) of N-(1-adamantylcarbonyl)-L-alanyl-L-proline ethylamide of melting point 116°-118° C; [α]D20 =-88.1° (c=0.99% in methanol).

Aufarbeitung

customevaporated to dryness
dissolutionThe oily residue was dissolved in ethyl acetate
washthe solution washed successively with 0.5-N hydrochloric acid, water, 5% sodium bicarbonate solution and water
dry with materialdried over sodium sulphate
customevaporated
customThe resulting oil was crystallised from ethyl acetate/petroleum ether

Quellen und Nachweise

ORD-Eintrag: ord-e94567f951974e3e91e1002d8f91b1cb
Quelldatensatz: uspto-grants-1979_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04176116

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