Reaktion #474135

ord-829a473394e04ffb9720d484c9e58e3c

Reaktionsgleichung

NC[C@H]1CC[C@H](C(=O)O)CC1
tranexamic acid
CCCC(=O)OC(CC)OC(=O)ON1C(=O)CCC1=O
1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxy]propyl butanoate
→
CCCC(=O)OC(CC)OC(=O)NC[C@H]1CC[C@H](C(=O)O)CC1
title compound 29
Ausbeute 62.0%
CCCC(=O)OC(CC)OC(=O)NC[C@H]1CC[C@H](C(=O)O)CC1
trans-4-{[1-(Butanoyloxy)propoxycarbonyl]aminomethyl}-Cyclohexanecarboxylic Acid
Ausbeute 62.0%

Edukte

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

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]propyl butanoate (575 mg, 2.0 mmol) were reacted in the MTBE/acetone/water mixture (16 mL) to yield the title compound 29 (408 mg, 62% yield) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (400 MHz, DMSO-d6): δ=0.81-0.94 (br. m, 8H), 1.17-1.38 (br. m, 3H), 1.47-1.58 (m, 2H), 1.64-1.75 (m, 4H), 1.83-1.92 (br. m, 2H), 2.10 (tt, J=12.0, 3/6 Hz, 1H), 2.26 (t, J=7.2 Hz, 2H), 2.75-2.88 (m, 2H), 6.55 (t, J=5.2 Hz, 1H), 7.42 (t, J=5.6 Hz, 1H), 11.97 (br. s, 1H). MS (ESI) m/z 352.18 (M+Na)+; 328.14 (M−H)−.

Quelle

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