1-((((2,5-Dioxo-1-pyrrolidinyl)oxy)carbonyl)oxy)ethyl 2-methylpropanoate → HCID 178471731, compound

HRID 734916Notes

Reaction equation

HRID 734916 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])[C:14]([O:16][CH:17]([O:19][C:20](ON1C(=O)CCC1=O)=[O:21])[CH3:18])=[O:15]>>[CH3:12][CH:13]([CH3:30])[C:14]([O:16][CH:17]([O:19][C:20]([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:21])[CH3:18])=[O:15]

Participants

3

Reactant 2

HCID 448144601-((((2,5-Dioxo-1-pyrrolidinyl)oxy)carbonyl)oxy)ethyl 2-methylpropanoateHCID 178511262HCID 178511262, compound

Product 1

HCID 178471731HCID 178471731, compoundYield 53%

Procedure

Following the general nucleophilic carbamoylation procedure, tranexamic acid and 1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxy]ethyl 2-methylpropanoate were reacted to yield the title compound 13 (333 mg, 53% yield) as a colorless powder after work-up and mass-guided preparative HPLC purification. 1H NMR (400 MHz, DMSO-d6): d=0.82-0.94 (br. m, 2H), 1.058 (d, J=6.4 Hz, 3H), 1.062 (d, J=6.8 Hz, 3H), 1.17-1.36 (br. m, 3H), 1.38 (d, J=5.6 Hz, 3H), 1.65-1.73 (br. m, 2H), 1.83-1.91 (br. m, 2H), 2.10 (tt, J=12.0, 3.6 Hz, 1H), 2.49 (hept., J=6.8 Hz, 1H), 2.77-2.85 (br. m, 2H), 6.62 (q, J=5.2 Hz, 1H), 7.45 (t, J=6.0 Hz, 1H), 11.97 (br. s, 1H). MS (ESI) m/z 338.08 (M+Na)+; 314.01 (M−H)−.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-398863135a61425ea0b1e25932aaa253
Source dataset
uspto-grants-2009_09
Patent number
US07592369B2

Reaction notes

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