Reaktion #474151

ord-6ad18bab68e44e85a98850e5790fa822

Reaktionsgleichung

NC[C@H]1CC[C@H](C(=O)O)CC1
tranexamic acid
CC(C)CC(=O)OC(OC(=O)ON1C(=O)CCC1=O)C(C)C
1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxyl]-2-methylpropyl 3-methylbutanoate
→
CC(C)CC(=O)OC(OC(=O)NC[C@H]1CC[C@H](C(=O)O)CC1)C(C)C
title compound 46
Ausbeute 12.0%
CC(C)CC(=O)OC(OC(=O)NC[C@H]1CC[C@H](C(=O)O)CC1)C(C)C
trans-4-{[1-(3-Methylbutanoyloxy)-2-methylpropoxycarbonyl]aminomethyl}-Cyclohexanecarboxylic Acid
Ausbeute 12.0%

Edukte

NC[C@H]1CC[C@H](C(=O)O)CC1
tranexamic acid
CC(C)CC(=O)OC(OC(=O)ON1C(=O)CCC1=O)C(C)C
1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxyl]-2-methylpropyl 3-methylbutanoate

Reagenzien

Keine

Lösungsmittel

CC(C)=O.COC(C)(C)C.O
MTBE acetone water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Following the general nucleophilic carbamoylation procedure, tranexamic acid (472 mg, 3.0 mmol) and 1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxyl]-2-methylpropyl 3-methylbutanoate (558 mg, 1.77 mmol) were reacted in the MTBE/acetone/water mixture (16 mL) to yield the title compound 46 (75 mg, 12% yield) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (400 MHz, DMSO-d6): δ=0.82-0.94 (br. m, 14H), 1.17-1.37 (m, 3H), 1.65-1.73 (br. m, 2H), 1.83-2.01 (br. m, 4H), 2.09 (tt, J=12.4, 3.6 Hz, 1H), 2.17 (d, J=6.6 Hz, 2H), 2.74-2.87 (br. m, 2H), 6.45 (d, J=4.8 Hz, 1H), 7.40 (t, J=6.0 Hz, 1H), 11.97 (br. s, 1H). MS (ESI) m/z 380.23 (M+Na)+; 356.18 (M−H)−.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08372881B2uspto-grants-2013_02