1-[(2,5-Dioxopyrrolidinyl)oxycarbonyloxy]ethyl pentanoate → HCID 178447566, compound

HRID 386939Notes

Reaction equation

HRID 386939 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:21][C:22](ON1C(=O)CCC1=O)=[O:23])[CH3:20])(=[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: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])[CH3:20])(=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 866102751-[(2,5-Dioxopyrrolidinyl)oxycarbonyloxy]ethyl pentanoateHCID 178511262HCID 178511262, compound

Product 1

HCID 178447566HCID 178447566, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 86610273MTBE acetone waterSolvent

Procedure

Following the general nucleophilic carbamoylation procedure, tranexamic acid (1.1 g, 7.0 mmol) and 1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxy]ethyl pentanoate (800 mg, 2.8 mmol) were reacted in the MTBE/acetone/water mixture (16 mL) to yield the title compound 12 (150 mg, 16% yield) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (400 MHz, DMSO-d6): δ=0.88-0.97 (m, 5H), 1.22-1.38 (br. m, 5H), 1.42 (d, J=5.2 Hz, 3H), 1.44-1.56 (m, 2H), 1.72-1.74 (m, 2H), 1.90-1.93 (m, 2H), 2.13 (tt, J=12, 3.6 Hz, 1H), 2.30 (t, J=7.2 Hz, 2H), 2.85 (t, J=6.4 Hz, 2H), 6.68 (q, J=5.6 Hz, 1H), 7.47 (t, J=6.0 Hz, 1H), 12.01 (br. s, 1H). MS (ESI) m/z 352.18 (M+Na)+; 328.14 (M−H)−.

Sources & evidence

ORD record
ord-e47eff84bd3345f2a234cb325ee8ce9e
Source dataset
uspto-grants-2013_02
Patent number
US08372881B2

Reaction notes

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