2-Bromoisovaleric acid → 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].[Na].Br[CH:12]([CH:16]([CH3:18])[CH3:17])[C:13]([OH:15])=[O:14]>>[F:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH:4][C@H:12]([C:13]([OH:15])=[O:14])[CH:16]([CH3:18])[CH3:17]

Participants

Reactant 3

HCID 112682-Bromoisovaleric acid

HCID 938984-Chloro-2-fluoroaniline

HCID 5360545Sodium

Product 1

HCID 54022058N-(2-fluoro-4-chlorophenyl)valine

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-dd65ce5e05084c77acfa3fa31a60f238
Source dataset: uspto-grants-1983_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04411912

Reaction notes

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