1-(2,5-Dioxoazolidinyloxycarbonyloxy)-2-methylpropyl 2-methylpropanoate → HCID 178454743, compound

HRID 734944Notes

Reaction equation

HRID 734944 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]([CH3:32])[C:14]([O:16][CH:17]([O:21][C:22](ON1C(=O)CCC1=O)=[O:23])[CH:18]([CH3:20])[CH3:19])=[O:15]>CC(OC)(C)C.CC(C)=O.O>[CH3:12][CH:13]([CH3:32])[C:14]([O:16][CH:17]([O:21][C:22]([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:23])[CH:18]([CH3:19])[CH3:20])=[O:15]

Participants

4

Reactant 2

HCID 448146361-(2,5-Dioxoazolidinyloxycarbonyloxy)-2-methylpropyl 2-methylpropanoateHCID 178511262HCID 178511262, compound

Product 1

HCID 178454743HCID 178454743, compoundYield 71%

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]-2-methylpropyl 2-methylpropanoate (603 mg, 2.0 mmol) were reacted in the MTBE/acetone/water mixture (16 mL) to yield the title compound 44 (486 mg, 71% 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, 8H), 1.06 (d, J=6.8 Hz, 3H), 1.08 (d, J=7.2 Hz, 3H), 1.16-1.38 (br. m, 3H), 1.64-1.73 (br. m, 2H), 1.82-1.92 (br. m, 3H), 2.10 (tt, J=12.0, 3.6 Hz, 1H), 2.52 (hept., J=6.8 Hz, 1H), 2.74-2.87 (br. m, 2H), 6.42 (d, J=5.2 Hz, 1H), 7.40 (t, J=6.0 Hz, 1H), 11.97 (br. s, 1H). MS (ESI) m/z 366.08 (M+Na)+; 342.04 (M−H)−.

Sources & evidence

ORD record
ord-5c9f50b721be45368578508c9749e1dd
Source dataset
uspto-grants-2009_09
Patent number
US07592369B2

Reaction notes

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