2-Bromoisovaleric acid → N-(2-fluoro-4-chlorophenyl)valine

Reaction equation

[K].Br[CH:3]([CH:7]([CH3:9])[CH3:8])[C:4]([OH:6])=[O:5].[F:10][C:11]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:12]=1[NH2:13]>>[F:10][C:11]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:12]=1[NH:13][C@H:3]([C:4]([OH:6])=[O:5])[CH:7]([CH3:9])[CH3:8]

Participants

Reactant 3

HCID 112682-Bromoisovaleric acid

HCID 938984-Chloro-2-fluoroaniline

HCID 5462222Potassium

Product 1

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

Procedure

N-(2-fluoro-4-chlorophenyl)valine and m-phenoxybenzyl bromide are reacted using the process of Example 42 to yield the m-phenoxybenzyl ester of N-(2-fluoro-4-chlorophenyl)valine, MS m/e 427.1 (M+, 4.1), 200 (100). N-(2-fluoro-4-chlorophenyl)valine is prepared by heating the potassium salt of α-bromoisovaleric acid and 2-fluoro-4-chloroaniline neat at 130° for about 2 hours.

Sources & evidence

ORD record: ord-9d871a72a40245d5b892ae188db456d3
Source dataset: uspto-grants-1983_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04411912

Reaction notes

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