Reaktion #474114

ord-c7be0af55427457ba81c66b0df9f0fbf

Reaktionsgleichung

NC[C@H]1CC[C@H](C(=O)O)CC1
tranexamic acid
CC(C)CC(=O)OCOC(=O)ON1C(=O)CCC1=O
1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxy]methyl 3-methylbutanoate
→
CC(C)CC(=O)OCOC(=O)NC[C@H]1CC[C@H](C(=O)O)CC1
title compound 5
Ausbeute 49.1%
CC(C)CC(=O)OCOC(=O)NC[C@H]1CC[C@H](C(=O)O)CC1
trans-4-{[(3-Methylbutanoyloxy)methoxycarbonyl]aminomethyl}-Cyclohexanecarboxylic Acid
Ausbeute 49.1%

Edukte

NC[C@H]1CC[C@H](C(=O)O)CC1
tranexamic acid
CC(C)CC(=O)OCOC(=O)ON1C(=O)CCC1=O
1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxy]methyl 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 (472 mg, 3.0 mmol) and 1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxy]methyl 3-methylbutanoate (547 mg, 2.0 mmol) were reacted in the MTBE/acetone/water mixture (16 mL) to yield the title compound 5 (310 mg, 49% yield) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (400 MHz, DMSO-d6): δ=0.86-0.94 (br. m, 8H), 1.17-1.38 (br. m, 3H), 1.64-1.72 (br. m, 2H), 1.83-1.91 (br. m, 2H), 1.96 (hept., J=7.2 Hz, 1H), 2.09 (tt, J=12.4, 3.6 Hz, 1H), 2.21 (d, J=6.8 Hz, 2H), 2.78-2.86 (br. m, 2H), 5.61 (s, 2H), 7.55 (t, J=5.6 Hz, 1H), 11.99 (br. s, 1H). MS (ESI) m/z 316.11 (M+H)+; 314.07 (M−H−).

Quelle

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