Reaktion #474153

ord-87b8f23b069443e6b54ff96d237ab167

Reaktionsgleichung

NC[C@H]1CC[C@H](C(=O)O)CC1
tranexamic acid
CC(C)C(OC(=O)ON1C(=O)CCC1=O)OC(=O)C1CCCCC1
1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxy]-2-methylpropyl cyclohexanecarboxylate
→
CC(C)C(OC(=O)NC[C@H]1CC[C@H](C(=O)O)CC1)OC(=O)C1CCCCC1
title compound 48
Ausbeute 27.0%
CC(C)C(OC(=O)NC[C@H]1CC[C@H](C(=O)O)CC1)OC(=O)C1CCCCC1
trans-4-{[1-(Cyclohexylcarbonyloxy)-2-methylpropoxycarbonyl]aminomethyl}-Cyclohexanecarboxylic Acid
Ausbeute 27.0%

Edukte

NC[C@H]1CC[C@H](C(=O)O)CC1
tranexamic acid
CC(C)C(OC(=O)ON1C(=O)CCC1=O)OC(=O)C1CCCCC1
1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxy]-2-methylpropyl cyclohexanecarboxylate

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 (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 L) 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)31.

Quelle

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