HCID 86610285, compound → HCID 178451010, compound

HRID 386961Notes

Reaction equation

HRID 386961 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]([CH3:33])[CH2:14][C:15]([O:17][CH:18]([O:22][C:23](ON1C(=O)CCC1=O)=[O:24])[CH2:19][CH2:20][CH3:21])=[O:16]>CC(OC)(C)C.CC(C)=O.O>[CH3:33][CH:13]([CH3:12])[CH2:14][C:15]([O:17][CH:18]([O:22][C:23]([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:24])[CH2:19][CH2:20][CH3:21])=[O:16]

Participants

4

Reactant 2

HCID 86610285HCID 86610285, compoundHCID 178511262HCID 178511262, compound

Product 1

HCID 178451010HCID 178451010, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 86610273MTBE acetone waterSolvent

Procedure

Following the general nucleophilic carbamoylation procedure, tranexamic acid (800 mg, 5.0 mmol) and 1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxy]butyl 3-methylbutanoate (700 mg, 2.2 mmol) were reacted in the MTBE/acetone/water mixture (16 mL) to yield the title compound 37 (120 mg, 15% yield) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (400 MHz, DMSO-d6): δ=0.87-0.95 (m, 11H), 1.21-1.41 (br. m, 5H), 1.68-1.73 (m, 4H), 1.89-2.02 (m, 3H), 2.10-2.22 (m, 3H), 2.80-2.89 (m, 2H), 6.65 (t, J=5.6 Hz, 1H), 7.45 (t, J=6.0 Hz, 1H), 12.04 (s, 1H). MS (ESI) m/z 380.23 (M+Na)+; 356.18 (M−H)−.

Sources & evidence

ORD record
ord-acabdbab021049dc910264e76d18c527
Source dataset
uspto-grants-2013_02
Patent number
US08372881B2

Reaction notes

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