Reaktionsgleichung
[CH:1]1([NH:7][C:8](=[O:16])[NH:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N=C=NCCCN(C)C)C.C[O:29][C:30](=[O:41])[C@H:31]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=1)[NH2:32].C(N(C(C)C)CC)(C)C.[OH-].[Na+].Cl>CN(C=O)C.C(O)(=O)C.CO>[CH:1]1([NH:7][C:8](=[O:16])[NH:9][CH2:10][CH2:11][CH2:12][C:13]([NH:32][CH:31]([CH2:33][C:34]2[CH:35]=[CH:36][C:37]([OH:40])=[CH:38][CH:39]=2)[C:30]([OH:41])=[O:29])=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1Komponenten
Edukt 6
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
To a solution of 632 (0.45 g, 2.0 mmol) and 1-ethyl-3-(3-(dimethylamino)-propyl) carbodiimide (0.5 g, 2.2 mmol) in 15 mL of DMF, 0.53 g (2.3 mmol) of tyrosine methyl ester and 2.4 mmol of diisopropylethylamine were added. The mixture was heated at 60° C. for 6 h. Then, 50 mL of 0.1 N NaOH were added and the mixture was left at room temperature overnight. The reaction mixture was then acidified with concentrated HCl and extracted twice with a 2:1 mixture of chloroform:methanol. The organic phases were pooled, dried and evaporated. The residue was purified by chromatography on a silica column (5×4 cm). Elution with a 75:25:1 mixture of ethyl acetate:methanol:acetic acid yielded 140 mg (yield: 18%) of the target product as a brown oily liquid. LC-MS-ES negative mode: 390.3 (100%, [M−H]−), 290.9 (10%, (M−C6H10N]−), 264.9 (5%, [M−C7H12NO]−); positive mode: 392.5 (40%, [M+H]+), 264.95 (100%, [M−C7H10NO]+).
Aufarbeitung
- extractionextracted twice with a 2:1 mixture of chloroform
- customdried
- customevaporated
- customThe residue was purified by chromatography on a silica column (5×4 cm)
- washElution
- additionwith a 75:25:1 mixture of ethyl acetate
Quellen und Nachweise
- ORD-Eintrag
- ord-9a465793ebdb4a228f522a838fecc3d6
- Quelldatensatz
- uspto-grants-2013_07
- Patentnummer
- US08476043B2
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