3-Oxo-3-{[3-(trifluoromethyl)phenyl]amino}propanoic acid → HCID 54697511, compound
Reaction equation
[O:1]=[C:2]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)[CH2:3][C:4]([OH:6])=O>O>[OH:6][C:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:11][CH:12]=2)[NH:7][C:2](=[O:1])[CH:3]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
A suspension of 3-oxo-3-{[3-(trifluoromethyl)phenyl]amino}propanoic acid (3.26 g; 13.0 mmol; 1 eq) in polyphosphoric acid (26.4 g) is allowed to stir for 4 hours at 140° C. The mixture becomes limpid after 1 h30 stirring. After cooling to room temperature, the orange solution is taken-up in water (100 mL) and sonicated for 5 minutes. The resulting fine powder is filtrated and washed with cold water (4×20 mL). The solid is taken up several times in ethanol (3×100 mL) and concentrated to afford the title compound as a dry light orange powder (2.19 g; 9.6 mmol; 74%).
Workup
- temperatureAfter cooling to room temperature
- customsonicated for 5 minutes
- filtrationThe resulting fine powder is filtrated
- washwashed with cold water (4×20 mL)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-beb65cbde4dc4faf92738aba8101a18e
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08513250B2
Reaction notes
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