4-Chloro-2-fluoroaniline → N-(2-fluoro-4-chlorophenyl)valine
Reaction equation
[F:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH2:4].Br[CH:11]([CH:31]([CH3:33])[CH3:32])[C:12]([O:14]C(C#N)C1C=CC=C(OC2C=CC=CC=2)C=1)=[O:13]>>[F:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH:4][C@H:11]([C:12]([OH:14])=[O:13])[CH:31]([CH3:33])[CH3:32]Participants
3
Procedure
Following the procedure of Example 6, 2-fluoro-4-chloroaniline is reacted with m-phenoxy-α-cyanobenzyl α-bromoisovalerate to give the m-phenoxy-α-cyanobenzyl ester of N-(2-fluoro-4-chlorophenyl)valine, MS m/e 452 (M+). Alternatively 2-fluoro-4-chloroaniline is reacted with the sodium salt of α-bromoisovaleric acid to give N-(2-fluoro-4-chlorophenyl)valine, which is then esterified using m-phenoxy-α-cyanobenzyl bromide or mesylate.
Sources & evidence
- ORD record
- ord-291d0383b24249cab1ac95ecd857a6be
- Source dataset
- uspto-grants-1983_10