(S)-3-(3-nitrophenyl)-3-phenylacetylaminopropionic acid → (s)-3-Amino-3-(3-nitrophenyl)propionic acid

HRID 1368912Notes

Reaction equation

HRID 1368912 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C@@H:10]([NH:15]C(=O)CC2C=CC=CC=2)[CH2:11][C:12]([OH:14])=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]>Cl>[NH2:15][C@H:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH2:11][C:12]([OH:14])=[O:13]

Participants

3

Reactant 1

HCID 711905(S)-3-(3-nitrophenyl)-3-phenylacetylaminopropionic acid

Product 1

HCID 706689(s)-3-Amino-3-(3-nitrophenyl)propionic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(S)-3-(3-nitrophenyl)-3-phenylacetylaminopropionic acid is treated with 10 ml of 6N HCl solution. (S)-3-amino-3-(3-nitrophenyl)propionic acid is obtained and is reacted further in analogy to the R enantiomer. This gives (S)-3-{2-[4-(4-methylpyridin-2-ylamino)butyrylamino]acetylamino}-3-(3-nitrophenyl)propionic acid, (S)-3-{2-[4-(4-methylpyridin-2-ylamino)butyrylamino]acetylamino}-3-(3-nitrophenyl propionic acid sodium salt, (S)-3-{2-[4-(4-methylpyridin-2-ylamino)butyrylamino]acetylamino}-3-(3-nitrophenyl)propionic acid trifluoroacetate, RT* 16.89 min, FAB-MS (M+H)+ 444.

Sources & evidence

ORD record
ord-cd63b630b65a48349ffa25259de9925d
Source dataset
uspto-grants-2003_06
Patent number
US06576637B1

Reaction notes

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