Acetic Acid → (Z)-Ethyl 3-((2-amino-2-oxoethyl)amino)-3-(2-(2-hydroxyethoxy)phenyl)acrylate

HRID 75554

Reaction equation

[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=O)[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].Cl.[NH2:20][CH2:21][C:22]([NH2:24])=[O:23].C(N(CC)CC)C.C(O)(=O)C.C(=O)(O)[O-].[Na+]>CO>[NH2:24][C:22](=[O:23])[CH2:21][NH:20]/[C:11](/[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[O:4][CH2:3][CH2:2][OH:1])=[CH:12]\[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of ethyl 3-(2-(2-hydroxyethoxy)phenyl)-3-oxopropanoate (2 g, 7.94 mmol) and glycinamide hydrochloride (3.5 g, 31.7 mmol) in methanol (20 mL) was added triethylamine (3.21 g, 31.7 mmol) at room temperature. The mixture was stirred at 40° C. for 20 min. Acetic acid (1.9 g, 31.7 mmol) was added, and the mixture was stirred at 80° C. for 18 hours. The reaction mixture was cooled to room temperature and saturated sodium bicarbonate (200 mL) was added. The organic layer was separated, dried (Na2SO4) and concentrated to give a yellow solid. The solid was washed with EtOAc (20 mL), and the residue was dried under reduced pressure to give the title compound as a white solid. This material was used without further purification.

Workup

stirringthe mixture was stirred at 80° C. for 18 hours
temperatureThe reaction mixture was cooled to room temperature
customThe organic layer was separated
dry with materialdried (Na2SO4)
concentrationconcentrated
customto give a yellow solid
washThe solid was washed with EtOAc (20 mL)
customthe residue was dried under reduced pressure

Sources & evidence

ORD record: ord-ffdb5ae04a694f5bac5a85efe7d4ce8c
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835449B2

Linked notes

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