Reaktion #474115

ord-7cc28c0eef1b49c2bacff533d342c69a

Reaktionsgleichung

NC[C@H]1CC[C@H](C(=O)O)CC1
tranexamic acid
CC(C)(C)C(=O)OCOC(=O)ON1C(=O)CCC1=O
1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxy]methyl 2,2-dimethylpropanoate
→
CC(C)(C)C(=O)OCOC(=O)C(N)[C@H]1CC[C@H](C(=O)O)CC1
title compound 6
Ausbeute 76.0%
CC(C)(C)C(=O)OCOC(=O)C(N)[C@H]1CC[C@H](C(=O)O)CC1
trans-4-{[(2,2-Dimethylpropanoyloxy)methoxycarbonyl]-aminomethyl}-Cyclohexanecarboxylic Acid
Ausbeute 76.0%

Edukte

NC[C@H]1CC[C@H](C(=O)O)CC1
tranexamic acid
CC(C)(C)C(=O)OCOC(=O)ON1C(=O)CCC1=O
1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxy]methyl 2,2-dimethylpropanoate

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)oxycarbonyloxy]methyl 2,2-dimethylpropanoate (547 mg, 2.0 mmol) were reacted in the MTBE/acetone/water mixture (16 mL) to yield the title compound 6 (476 mg, 76% 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, 2H), 1.13 (s, 9H), 1.17-1.38 (br. m, 3H), 1.64-1.72 (br. m, 2H), 1.82-1.91 (br. m, 2H), 2.09 (tt, J=12.0, 3.6 Hz, 1H), 2.78-2.87 (br. m, 2H), 5.61 (s, 2H), 7.54 (t, J=5.6 Hz, 1H), 11.98 (br. s, 1H). MS (ESI) m/z 316.11 (M+H)+; 314.01 (M−H)−.

Quelle

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