Acetic Acid → (Z)-Ethyl 3-((2-amino-2-oxoethyl)amino)-3-(5-chloro-2-methoxyphenyl)acrylate

HRID 77529

Reaction equation

C[O-].[Na+].Cl.[NH2:5][CH2:6][C:7]([NH2:9])=[O:8].C(O)(=O)C.[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([O:29][CH3:30])=[C:19]([C:21](=O)[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:20]=1>CO>[NH2:9][C:7](=[O:8])[CH2:6][NH:5]/[C:21](/[C:19]1[CH:20]=[C:15]([Cl:14])[CH:16]=[CH:17][C:18]=1[O:29][CH3:30])=[CH:22]\[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

Conditions

Temperature: 65 °C

Procedure

A 5-L reaction vessel was charged with methanol (3.3 L), sodium methoxide (102.4 g, 1.8 moles), and glycinamide hydrochloride (202 g, 1.8 moles). The mixture was heated at 65° C. for 1 hour before cooling to 50° C. and adding acetic acid (514.25 mmoles, 30.88 g, 29.47 mL) and ethyl 3-(5-chloro-2-methoxyphenyl)-3-oxopropanoate (300 g, 1.03 mole). After heating to reflux for 16 hours, the reaction mixture was stirred as it was cooled to 10° C. After 30 min the resulting solid was collected by vacuum filtration, pulling dry to form a cake that was dried in a vacuum oven (20 mm Hg, 65° C.) for 14 hours to afford the title compound (339.4 g).

Workup

temperaturebefore cooling to 50° C.
temperatureAfter heating
temperatureto reflux for 16 hours
temperaturewas cooled to 10° C
filtrationAfter 30 min the resulting solid was collected by vacuum filtration
custompulling dry
customto form a cake that
customwas dried in a vacuum oven (20 mm Hg, 65° C.) for 14 hours

Sources & evidence

ORD record: ord-8372f552ad434702acb95e0b5fb4bee4
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841314B2

Linked notes

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