1-[(2,5-Dioxopyrrolidinyl)oxycarbonyloxy]ethyl cyclohexanecarboxylate → HCID 178473495, compound

HRID 386946Notes

Reaction equation

HRID 386946 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].[CH:12]1([C:18]([O:20][CH:21]([O:23][C:24](ON2C(=O)CCC2=O)=[O:25])[CH3:22])=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>CC(OC)(C)C.CC(C)=O.O>[CH:12]1([C:18]([O:20][CH:21]([O:23][C:24]([NH:11][CH2:10][C@H:2]2[CH2:3][CH2:4][C@H:5]([C:7]([OH:9])=[O:8])[CH2:6][CH2:1]2)=[O:25])[CH3:22])=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 866102781-[(2,5-Dioxopyrrolidinyl)oxycarbonyloxy]ethyl cyclohexanecarboxylateHCID 178511262HCID 178511262, compound

Product 1

HCID 178473495HCID 178473495, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 86610273MTBE acetone waterSolvent

Procedure

Following the general nucleophilic carbamoylation procedure, tranexamic acid (780 mg, 5.0 mmol) and 1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxy]ethyl cyclohexanecarboxylate (700 mg, 2.2 mmol) were reacted in the MTBE/acetone/water mixture (16 mL) to yield the title compound 22 (200 mg, 26% yield) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (400 MHz, DMSO-d6): δ=0.87-0.99 (m, 2H), 1.20-1.44 (br. m, 11H), 1.58-1.81 (m, 7H), 1.89-1.92 (m, 2H), 2.13 (tt, J=12, 3.6 Hz, 1H), 2.27-2.35 (m, 1H), 2.79-2.90 (m, 2H), 6.66 (q, J=5.6 Hz, 1H), 7.48 (t, J=6.0 Hz, 1H), 12.05 s, 1H). MS (ESI) m/z 378.13 (M+Na)+; 354.15 (M−H)−.

Sources & evidence

ORD record
ord-028da0b5b8474b21b26f49bdff09a492
Source dataset
uspto-grants-2013_02
Patent number
US08372881B2

Reaction notes

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