1-[(2,5-Dioxopyrrolidinyl)oxycarbonyloxy]methyl 3-methylbutanoate → HCID 178447593, compound

HRID 386932Notes

Reaction equation

HRID 386932 reaction equation
[CH2:1]1[CH2:6][C@H:5]([C:7]([OH:9])=[O:8])[CH2:4][CH2:3][C@H:2]1[CH2:10][NH2:11].[CH3:12][CH:13]([CH3:30])[CH2:14][C:15]([O:17][CH2:18][O:19][C:20](ON1C(=O)CCC1=O)=[O:21])=[O:16]>CC(OC)(C)C.CC(C)=O.O>[CH3:12][CH:13]([CH3:30])[CH2:14][C:15]([O:17][CH2:18][O:19][C:20]([NH:11][CH2:10][C@H:2]1[CH2:3][CH2:4][C@H:5]([C:7]([OH:9])=[O:8])[CH2:6][CH2:1]1)=[O:21])=[O:16]

Participants

4

Reactant 2

HCID 866102721-[(2,5-Dioxopyrrolidinyl)oxycarbonyloxy]methyl 3-methylbutanoateHCID 178511262HCID 178511262, compound

Product 1

HCID 178447593HCID 178447593, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 86610273MTBE acetone waterSolvent

Procedure

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−).

Sources & evidence

ORD record
ord-c7be0af55427457ba81c66b0df9f0fbf
Source dataset
uspto-grants-2013_02
Patent number
US08372881B2

Reaction notes

Loading…