(-)-2-Aminobutyric acid → (2S)-2-[(4-bromo-2-nitrophenyl)amino]butanoic acid

HRID 898270Notes

Reaction equation

HRID 898270 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[NH2:12][C@@H:13]([CH2:17][CH3:18])[C:14]([OH:16])=[O:15].FC1C=CC(N[C@H](CC)C(O)=O)=C([N+]([O-])=O)C=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C@@H:13]([CH2:17][CH3:18])[C:14]([OH:16])=[O:15])=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

4

Reactant 3

HCID 80283(-)-2-Aminobutyric acidHCID 27363284-Bromo-1-fluoro-2-nitrobenzeneHCID 69223325(R)-2-(4-fluoro-2-nitrophenylamino)-butyric acid

Product 1

HCID 69223203(2S)-2-[(4-bromo-2-nitrophenyl)amino]butanoic acid

Procedure

5-Bromo-2-fluoronitrobenzene was treated with (S)-2-aminobutyric acid according to the procedure for the preparation of (R)-2-(4-fluoro-2-nitrophenylamino)-butyric acid (see Example 1) to yield (2S)-2-[(4-bromo-2-nitrophenyl)amino]butanoic acid. MS (ESI) m/z 303/305 ([M+H]+); MS (ESI) m/z 301/303 ([M−H]−).

Sources & evidence

ORD record
ord-bacfeb73b14e4160a2ea018572548031
Source dataset
uspto-grants-2008_04
Patent number
US07351709B2

Reaction notes

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