HCID 86610289, compound → HCID 178447595, compound

HRID 504126Notes

Reaction equation

HRID 504126 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:18][CH:19]([O:23][C:24](ON1C(=O)CCC1=O)=[O:25])[CH:20]([CH3:22])[CH3:21])(=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16]>CC(OC)(C)C.CC(C)=O.O>[C:12]([O:18][CH:19]([O:23][C:24]([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:25])[CH:20]([CH3:22])[CH3:21])(=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 86610289HCID 86610289, compoundHCID 178511262HCID 178511262, compound

Product 1

HCID 178447595HCID 178447595, compound

Reagents, catalysts & solvents 1

HCID 86610273MTBE acetone waterSolvent

Procedure

Following the general nucleophilic carbamoylation procedure, tranexamic acid (700 mg, 4.5 mmol) and 1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxy]-2-methylpropyl pentanoate (500 mg, 1.6 mmol) were reacted in the MTBE/acetone/water mixture (16 mL) to yield the title compound 42 as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (400 MHz, DMSO-d6): δ=0.83-0.92 (br. m, 11H), 1.17-1.32 (br. m, 5H), 1.45-1.52 (m, 2H), 1.68 (d, J=12 Hz, 2H), 1.85-1.94 (br. m, 3H), 2.04-2.12 (m, 1H), 2.27-2.32 (br. m, 1H), 2.83 (td, J=7.2, 1.6 Hz, 2H), 2.78-2.82 (m, 2H), 6.42 (d, J=5.2 Hz, 1H), 7.38 (t, J=6.0 Hz, 1H), 11.97 (br. s, 1H). MS (ESI) m/z 380.16 (M+Na)+; 356.17 (M−H)−.

Sources & evidence

ORD record
ord-7870b3d6102d4a79b8caf8c301439867
Source dataset
uspto-grants-2010_08
Patent number
US07777070B2

Reaction notes

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