((((2,5-Dioxopyrrolidin-1-yl)oxy)carbonyl)oxy)methyl pivalate → HCID 178447592, compound

HRID 386933Notes

Reaction equation

HRID 386933 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][C:13]([CH3:30])([CH3:29])[C:14]([O:16][CH2:17][O:18][C:19](ON1C(=O)CCC1=O)=[O:20])=[O:15]>CC(OC)(C)C.CC(C)=O.O>[CH3:12][C:13]([CH3:30])([CH3:29])[C:14]([O:16][CH2:17][O:18][C:19]([CH:10]([NH2:11])[C@H:2]1[CH2:3][CH2:4][C@H:5]([C:7]([OH:9])=[O:8])[CH2:6][CH2:1]1)=[O:20])=[O:15]

Participants

4

Reactant 2

HCID 86610274((((2,5-Dioxopyrrolidin-1-yl)oxy)carbonyl)oxy)methyl pivalateHCID 178511262HCID 178511262, compound

Product 1

HCID 178447592HCID 178447592, compoundYield 76%

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 2,2-dimethylpropanoate (547 mg, 2.0 mmol) were reacted in the MTBE/acetone/water mixture (16 mL) to yield the title compound 6 (476 mg, 76% yield) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (400 MHz, DMSO-d6): δ=0.82-0.94 (br. m, 2H), 1.13 (s, 9H), 1.17-1.38 (br. m, 3H), 1.64-1.72 (br. m, 2H), 1.82-1.91 (br. m, 2H), 2.09 (tt, J=12.0, 3.6 Hz, 1H), 2.78-2.87 (br. m, 2H), 5.61 (s, 2H), 7.54 (t, J=5.6 Hz, 1H), 11.98 (br. s, 1H). MS (ESI) m/z 316.11 (M+H)+; 314.01 (M−H)−.

Sources & evidence

ORD record
ord-7cc28c0eef1b49c2bacff533d342c69a
Source dataset
uspto-grants-2013_02
Patent number
US08372881B2

Reaction notes

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