3-Nitrobenzoic acid → 3-Methylphenylalanine

Reaction equation

C[O:2][C:3](=[O:23])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[NH:5]C(C1C(C)=CC=CC=1Cl)=O.[N+]([C:27]1C=C(C=CC=1)C(O)=O)([O-])=O>>[CH3:27][C:21]1[CH:22]=[C:17]([CH:18]=[CH:19][CH:20]=1)[CH2:16][C@@H:4]([C:3]([OH:2])=[O:23])[NH2:5]

Participants

Reactant 2

HCID 84973-Nitrobenzoic acid

HCID 54163741HCID 54163741, compound

Product 1

HCID 27614943-Methylphenylalanine

Procedure

N-[1-(2-Chloro-6-methylphenyl)carbonyl]-4-[[2-(3-nitrophenyl))-1-oxoethyl]amino]-3-methyl-L-phenylalanine was prepared from 4-amino-3-methyl-N-[[(2-chloro-6-methylphenyl)carbonyl]-L-phenylalanine methyl ester (52 mg) and 3-nitrobenzoic acid (32 mg, 0.19 mmol) using the procedure described in example 120 to give 15 mg of a white powder. HR MS (C25H22N3O6Cl): Obs. Mass 496.1288. Calcd. Mass 496.1288 (M+H).

Sources & evidence

ORD record: ord-04fe5551ef5447c7a898d76cfdc4a0d5
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06229011B1

Reaction notes

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