HCID 86610286, compound → HCID 178453631, compound

HRID 386962Notes

Reaction equation

HRID 386962 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]([CH3:33])([CH3:32])[C:14]([O:16][CH:17]([O:21][C:22](ON1C(=O)CCC1=O)=[O:23])[CH2:18][CH2:19][CH3:20])=[O:15]>CC(OC)(C)C.CC(C)=O.O>[CH3:32][C:13]([CH3:12])([CH3:33])[C:14]([O:16][CH:17]([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])[CH2:18][CH2:19][CH3:20])=[O:15]

Participants

4

Reactant 2

HCID 86610286HCID 86610286, compoundHCID 178511262HCID 178511262, compound

Product 1

HCID 178453631HCID 178453631, compoundYield 12%

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 2,2-dimethylpropanoate (700 mg, 2.2 mmol) were reacted in the MTBE/acetone/water mixture (16 mL) to yield the title compound 38 (90 mg, 12% yield) as a white powder after work-up and mass-guided preparative HPLC purification, 1H NMR (400 MHz, DMSO-d6): δ=0.87-0.99 (m, 5H), 1.12-1.38 (br. m, 14H), 1.69-1.74 (m, 4H), 1.89-1.92 (m, 2H), 2.13 (tt, J=12, 3.2 Hz, 1H), 2.78-2.91 (m, 2H), 6.61 (t, J 5.6 Hz, 1H), 7.47 (t, J=6.0 Hz, 1H), 12.04 (s, 1H), MS (ESI) m/z 380.22 (M+Na)+; 356.18 (M−H)−.

Sources & evidence

ORD record
ord-29454f5d58334a6c9295c5d23c893549
Source dataset
uspto-grants-2013_02
Patent number
US08372881B2

Reaction notes

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