HCID 86610290, compound → HCID 178454744, compound

HRID 734943Notes

Reaction equation

HRID 734943 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:17][CH:18]([O:22][C:23](ON1C(=O)CCC1=O)=[O:24])[CH:19]([CH3:21])[CH3:20])(=[O:16])[CH2:13][CH2:14][CH3:15]>CC(OC)(C)C.CC(C)=O.O>[C:12]([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])[CH:19]([CH3:21])[CH3:20])(=[O:16])[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 86610290HCID 86610290, compoundHCID 178511262HCID 178511262, compound

Product 1

HCID 178454744HCID 178454744, compoundYield 75%

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 butanoate (602 mg, 2.0 mmol) were reacted in the MTBE/acetone/water mixture (16 mL) to yield the title compound 43 (513 mg, 75% yield) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (400 MHz, DMSO-d6): δ=0.83-0.95 (br. m, 11H), 1.17-1.38 (br. m, 3H), 1.48-1.58 (m, 2H), 1.65-1.73 (br. m, 2H), 1.83-1.98 (br. m, 3H), 2.10 (tt, J=12.0, 3.2 Hz, 1H), 2.21-2.32 (br. m, 2H), 2.75-2.87 (br. m, 2H), 6.44 (d, J=5.6 Hz, 1H), 7.40 (t, J=6.0 Hz), 11.97 (br. s, 1H). MS (ESI) m/z 366.21 (M+Na)+; 342.16 (M−H)−.

Sources & evidence

ORD record
ord-d0e339449eda4e8ebcd76cc0706e55b1
Source dataset
uspto-grants-2009_09
Patent number
US07592369B2

Reaction notes

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