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

HRID 648248Notes

Reaction equation

HRID 648248 reaction equation
Br[CH:2]([CH:6]([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4].[F:9][C:10]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:11]=1[NH2:12].C(C(Br)C1C=CC=C(OC2C=CC=CC=2)C=1)#C>>[F:9][C:10]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:11]=1[NH:12][C@H:2]([C:3]([OH:5])=[O:4])[CH:6]([CH3:8])[CH3:7]

Participants

4

Reactant 3

HCID 112682-Bromoisovaleric acidHCID 679842-Fluoro-4-methylanilineHCID 20482714alpha-Ethynyl-m-phenoxybenzyl bromide

Product 1

HCID 54059120N-(2-fluoro-4-methylphenyl)valine

Procedure

N-(2-fluoro-4-methylphenyl)valine is prepared from α-bromoisovaleric acid and 2-fluoro-4-methylaniline and then reacted with α-ethynyl-m-phenoxybenzyl bromide to yield the α-ethynyl-m-phenoxybenzyl ester of N-(2-fluoro-4-methylphenyl)valine, MS m/e 431 (M+, 180).

Sources & evidence

ORD record
ord-ee147b63d6714c55b61f35210653de27
Source dataset
uspto-grants-1983_10
Patent number
US04411912

Reaction notes

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