HCID 86610282, compound → HCID 178454706, compound

HRID 386953Notes

Reaction equation

HRID 386953 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:21][C:22](ON1C(=O)CCC1=O)=[O:23])[CH2:19][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: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])[CH2:19][CH3:20])(=[O:16])[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 86610282HCID 86610282, compoundHCID 178511262HCID 178511262, compound

Product 1

HCID 178454706HCID 178454706, compoundYield 62%

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]propyl butanoate (575 mg, 2.0 mmol) were reacted in the MTBE/acetone/water mixture (16 mL) to yield the title compound 29 (408 mg, 62% yield) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (400 MHz, DMSO-d6): δ=0.81-0.94 (br. m, 8H), 1.17-1.38 (br. m, 3H), 1.47-1.58 (m, 2H), 1.64-1.75 (m, 4H), 1.83-1.92 (br. m, 2H), 2.10 (tt, J=12.0, 3/6 Hz, 1H), 2.26 (t, J=7.2 Hz, 2H), 2.75-2.88 (m, 2H), 6.55 (t, J=5.2 Hz, 1H), 7.42 (t, J=5.6 Hz, 1H), 11.97 (br. s, 1H). MS (ESI) m/z 352.18 (M+Na)+; 328.14 (M−H)−.

Sources & evidence

ORD record
ord-829a473394e04ffb9720d484c9e58e3c
Source dataset
uspto-grants-2013_02
Patent number
US08372881B2

Reaction notes

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