1-({[(2,5-Dioxopyrrolidin-1-yl)oxy]carbonyl}oxy)propyl benzoate → HCID 178459856, compound

HRID 386956Notes

Reaction equation

HRID 386956 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].[C:12]([O:20][CH:21]([O:24][C:25](ON1C(=O)CCC1=O)=[O:26])[CH2:22][CH3:23])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CC(OC)(C)C.CC(C)=O.O>[C:12]([O:20][CH:21]([O:24][C:25]([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:26])[CH2:22][CH3:23])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 714270241-({[(2,5-Dioxopyrrolidin-1-yl)oxy]carbonyl}oxy)propyl benzoateHCID 178511262HCID 178511262, compound

Product 1

HCID 178459856HCID 178459856, compoundYield 93.4%

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]propyl benzoate (602 mg, 2.0 mmol) were reacted in the MTBE/acetone/water mixture (16 mL) to yield the title compound 32 (679 mg, 93% yield) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (400 MHz, DMSO-d6): δ=0.80-0.95 (br. m, 2H), 0.96 (t, J=7.6 Hz, 3H), 1.15-1.38 (br. m., 3H), 1.60-1.74 (m, 2H), 1.82-1.91 (m, 4H), 2.08 (tt, J=12.0, 3.2 Hz, 1H), 2.76-2.87 (br. m, 2H), 6.78 (t, J=5.6 Hz, 1H), 7.48-7.56 (br. m, 3H), 7.67 (tt, J=7.6, 1.2 Hz, 1H), 7.90-7.95 (m, 2H), 11.96 (br. s, 1H). MS (ESI) m/z 386.12 (M+Na)+; 362.14 (M−H)−.

Sources & evidence

ORD record
ord-c05612750ec8441fb35ae628c0b43e3c
Source dataset
uspto-grants-2013_02
Patent number
US08372881B2

Reaction notes

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