MTBE acetone water → HCID 178440862, compound

HRID 386950Notes

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][CH:13]([CH3:39])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([CH3:38])[C:22]([O:24][CH:25](OC(ON2C(=O)CCC2=O)=O)[CH3:26])=[O:23])=[CH:17][CH:16]=1.CC([O:44][CH3:45])(C)C.CC(C)=[O:48].O>>[CH3:39][CH:13]([CH3:12])[CH2:14][C:15]1[CH:16]=[CH:17][C:18]([CH:21]([CH3:38])[C:22]([O:24][CH2:25][CH2:26][O:48][C:45]([NH:11][CH2:10][C@H:2]2[CH2:3][CH2:4][C@H:5]([C:7]([OH:9])=[O:8])[CH2:6][CH2:1]2)=[O:44])=[O:23])=[CH:19][CH:20]=1

Participants

Reactant 3

HCID 86610273MTBE acetone water

HCID 86610280HCID 86610280, compound

HCID 178511262HCID 178511262, compound

Product 1

HCID 178440862HCID 178440862, compoundYield 47%

Procedure

Following the general nucleophilic carbamoylation procedure, tranexamic acid (629 mg, 4.0 mmol) and 1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxy]ethyl 2-[4-(2-methylpropyl)phenyl]propanoate (665 mg, 1.7 mmol) were reacted in the MTBE/acetone/water mixture (32 mL) to yield the title compound 26 (344 mg, 47% yield) as a colorless powder after work-up and mass-guided preparative HPLC purification. 1H NMR (400 MHz, DMSO-d6): δ=0.79-0.95 (m, 8H), 1.16-1.39 (m, 9H), 1.60-1.92 (m, 5H), 2.02-2.15 (m, 1 H), 2.38-2.44 (m, 2H), 2.70-2.86 (m, 2H), 3.68-3.76 (m, 1H), 6.62-6.72 (m, 1H), 7.04-7.18 (m, 4H), 7.32-7.50 (m, 1H), 11.98 (br. s, 1H). MS (ESI) m/z 456.24 (M+Na)+; 432.19 (M−H)−.

Sources & evidence

ORD record: ord-0fa79b01b5444c8b8aa925b3c5bb698a
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372881B2

Reaction notes

Loading…