L-Phenylalanine → (S)-N-(4-Nitro-phenyl)-L-alanine

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C@@H:11]([C:13]([OH:15])=[O:14])[CH3:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].N[C@H](C(O)=O)CC1C=CC=CC=1>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C@H:11]([C:13]([OH:15])=[O:14])[CH3:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

Reactant 2

HCID 6140L-Phenylalanine

HCID 20848020N-(4-Nitrophenyl)-D-alanine

Product 1

HCID 29891421(S)-N-(4-Nitro-phenyl)-L-alanineYield 77%

Procedure

The reaction described above for 4-nitrophenyl-D-alanine was repeated for the L isomer. About 125 grams of L-Phe was nitrated as described above and resulted in about 124 grams of 4-nitrophenyl-L-alanine (about 77% yield). [α]D =+6.8° (c=1.0 in 1N HCl).

Sources & evidence

ORD record: ord-890fb744721b449c8145a8574786bb4c
Source dataset: uspto-grants-1994_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05352796

Reaction notes

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