HCID 86610283, compound → HCID 178459858, compound

HRID 386955Notes

Reaction equation

HRID 386955 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][C:13]([CH3:32])([CH3:31])[C:14]([O:16][CH:17]([O:20][C:21](ON1C(=O)CCC1=O)=[O:22])[CH2:18][CH3:19])=[O:15]>CC(OC)(C)C.CC(C)=O.O>[CH3:31][C:13]([CH3:12])([CH3:32])[C:14]([O:16][CH:17]([O:20][C:21]([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:22])[CH2:18][CH3:19])=[O:15]

Participants

4

Reactant 2

HCID 86610283HCID 86610283, compoundHCID 178511262HCID 178511262, compound

Product 1

HCID 178459858HCID 178459858, compoundYield 45%

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 2,2-dimethylpropanoate (290 mg, 0.96 mmol) were reacted in the MTBE/acetone/water mixture (16 mL) to yield the title compound 31 (147 mg, 45% yield) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (400 MHz, DMSO-d6): δ=0.82-0.94 (br. m, 5H), 1.12 (s, 9H), 1.16-1.38 (m, 3H), 1.64-1.76 (m, 4H), 1.82-1.91 (br. m, 2H), 2.09 (tt, J=12.0, 3.2 Hz, 1H), 2.72-2.90 (m, 2H), 6.51 (t, J=5.6 Hz, 1H), 7.44 (t, J=6.0 Hz, 1H), 11.97 (br. s, 1H). MS (ESI) m/z 366.21 (M+Na)+; 342.16 (M−H)−.

Sources & evidence

ORD record
ord-89ca9b6ba9e84d62a0fc227ece9b8a21
Source dataset
uspto-grants-2013_02
Patent number
US08372881B2

Reaction notes

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