Reaktion #474126

ord-92e6fe7b09804b718642cc99da3c883f

Reaktionsgleichung

NC[C@H]1CC[C@H](C(=O)O)CC1
tranexamic acid
CC(C)CC(=O)OC(C)OC(=O)ON1C(=O)CCC1=O
1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxy]ethyl 3-methylbutanoate
→
CC(C)CC(=O)OC(C)OC(=O)NC[C@H]1CC[C@H](C(=O)O)CC1
title compound 19
Ausbeute 21.7%
CC(C)CC(=O)OC(C)OC(=O)NC[C@H]1CC[C@H](C(=O)O)CC1
trans-4-{[1-(3-Methylbutanoyloxy)ethoxycarbonyl]aminomethyl}-Cyclohexanecarboxylic Acid
Ausbeute 21.7%

Edukte

NC[C@H]1CC[C@H](C(=O)O)CC1
tranexamic acid
CC(C)CC(=O)OC(C)OC(=O)ON1C(=O)CCC1=O
1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxy]ethyl 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 (900 mg, 6 mmol) and 1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxy]ethyl 3-methylbutanoate (800 mg, 2.8 mmol) were reacted in the MTBE/acetone/water mixture (16 mL) to yield the title compound 19 (200 mg, 21% yield) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (400 MHz, DMSO-d6): δ=0.88-0.97 (m, 8H), 1.22-1.38 (br. m, 3H), 1.42 (d, J=5.2 Hz, 3H), 1.71-1.74 (m, 2H), 1.90-2.02 (br. m, 3H), 2.1-2.2 (br. m, 3H), 2.85 (t, J=6.4 Hz, 2H), 6.69 (q, J=5.6 Hz, 1H), 7.48 (t, J=6.0 Hz, 1H), 12.01 (br. s, 1H). MS (ESI) m/z 352.15 (M+Na)+; 328.14 (M−H)−.

Quelle

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