Glycine, N-(4-chlorophenyl)-, ethyl ester → (E)-ethyl 2-((4-chlorophenyl)(4,4,4-trifluoro-3-oxobut-1-en-1-yl)amino)acetate

HRID 2167399Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.C(O/[CH:18]=[CH:19]/[C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8](/[CH:18]=[CH:19]/[C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of ethyl 2-((4-chlorophenyl)amino)acetate (10.0 g, 46.8 mmol) and (E)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one (11.0 g, 65.5 mmol) in DCM (150 mL) was heated overnight at 50° C. The resulting mixture was concentrated and then triturated with 20% EtOAc/heptane and the resulting solid filtered and washed with heptane to yield (E)-ethyl 2-((4-chlorophenyl)(4,4,4-trifluoro-3-oxobut-1-en-1-yl)amino)acetate.

Workup

concentrationThe resulting mixture was concentrated
customtriturated with 20% EtOAc/heptane
filtrationthe resulting solid filtered
washwashed with heptane

Sources & evidence

ORD record: ord-2d110231f27c4eb3a7dc7a085e9ae8c8
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045454B2

Reaction notes

Loading…