Reaktion #474116

ord-f574e7209ccd4adb87cc028a80654e8c

Reaktionsgleichung

NC[C@H]1CC[C@H](C(=O)O)CC1
tranexamic acid
O=C(OCOC(=O)c1ccccc1)ON1C(=O)CCC1=O
1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxy]methyl benzoate
→
O=C(NC[C@H]1CC[C@H](C(=O)O)CC1)OCOC(=O)c1ccccc1
title compound 7
Ausbeute 66.3%
O=C(NC[C@H]1CC[C@H](C(=O)O)CC1)OCOC(=O)c1ccccc1
trans-4-{[(Benzoyloxy)methoxycarbonyl]aminomethyl}-Cyclohexanecarboxylic Acid
Ausbeute 66.3%

Edukte

NC[C@H]1CC[C@H](C(=O)O)CC1
tranexamic acid
O=C(OCOC(=O)c1ccccc1)ON1C(=O)CCC1=O
1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxy]methyl benzoate

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 benzoate (587 mg, 2.0 mmol) were reacted in the MTBE/acetone/water mixture (16 mL) to yield the title compound 7 (445 mg, 66% yield) a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (400 MHz, DMSO-d6): δ=0.83-0.95 (br. m, 2H), 1.16-1.39 (br. m, 3H), 1.65-1.72 (br. M, 2H), 1.82-1.91 (br. m, 2H), 2.09 (tt, J=12.4, 3.6 Hz, 1H), 2.81-2.88 (br. m, 2H), 5.88 (s, 2H), 7.50-7.57 (m, 2H), 7.61 (t, J=6.0 Hz, 1H), 7.65-7.70 (m, 1H), 7.93-7.97 (m, 2H), 11.96 (br. s, 1H). MS (ESI) m/z 336.01 (M+H)+; 333.98 (M−H)−.

Quelle

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