1-(2,5-Dioxoazolidinyloxycarbonyloxy)-2-methylpropyl cyclohexanecarboxylate → HCID 178453628, Verbindung

HRID 734948

Reaktionsgleichung

Reaktionsgleichung von HRID 734948
[CH2:1]1[CH2:6][C@H:5]([C:7]([OH:9])=[O:8])[CH2:4][CH2:3][C@H:2]1[CH2:10][NH2:11].[CH:12]1([C:18]([O:20][CH:21]([O:25][C:26](ON2C(=O)CCC2=O)=[O:27])[CH:22]([CH3:24])[CH3:23])=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>CC(OC)(C)C.CC(C)=O.O>[CH:12]1([C:18]([O:20][CH:21]([O:25][C:26]([NH:11][CH2:10][C@H:2]2[CH2:3][CH2:4][C@H:5]([C:7]([OH:9])=[O:8])[CH2:6][CH2:1]2)=[O:27])[CH:22]([CH3:23])[CH3:24])=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Komponenten

4

Edukt 2

HCID 866102931-(2,5-Dioxoazolidinyloxycarbonyloxy)-2-methylpropyl cyclohexanecarboxylateHCID 178511262HCID 178511262, Verbindung

Produkt 1

HCID 178453628HCID 178453628, VerbindungAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 86610273MTBE acetone waterLösungsmittel

Versuchsvorschrift

Following the general nucleophilic carbamoylation procedure, tranexamic acid (1.4 g, 8.0 mmol) and 1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxy]-2-methylpropyl cyclohexanecarboxylate (1.0 g, 2.9 mmol) were reacted in the MTBE/acetone/water mixture (16 mL) to yield the title compound 48 (300 mg, 27% yield) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (400 MHz, DMSO-d6): δ=0.83-0.92 (br. m, 8H), 1.15-1.35 (br. m, 8H), 1.54-1.95 (br. m, 10H), 2.08 (tt, J=12.0, 3.6 Hz, 1H), 2.27-2.32 (br. m, 1H), 2.74-2.83 (br. m, 2H), 6.41 (d, J=5.2 Hz, 1H), 7.39 (t, J=6.0 Hz, 1H), 11.97 (br. s, 1H). MS (ESI) m/z 406.14 (M+Na)+; 382.17 (M−H)−.

Quellen und Nachweise

ORD-Eintrag
ord-03217e379c094ac594754c73d415bb28
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592369B2

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