Methanol → Methyl 3-amino-3-(3-nitrophenyl)propanoate
Reaction equation
[NH2:1][C@@H:2]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:20]O>>[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1)[CH2:3][C:4]([O:6][CH3:20])=[O:5]Participants
Procedure
(R)-3-amino-3-(3-nitrophenyl)propionic acid is esterified in analogy to Example 2 by activation with thionyl chloride and reaction with methanol under standard conditions to give methyl 3-amino-3-(3-nitrophenyl)propionate, which is reacted with BOC-Gly-OH and 4-(4-methylpyridin-2-ylamino)butyric acid. Cleavage of the ester results in (R)-3-{2-[4-(4-methylpyridin-2-ylamino)butyrylamino]acetylamino}-3-(3-nitrophenyl)propionic acid. Use of an excess of NaOH results in the sodium salt of (R)-3-{2-[4-(4-methylpyridin-2-ylamino)butyrylamino]acetylamino}-3-(3-nitrophenyl)propionic acid. Preparative HPLC results in (R)-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-afa33b5bfc974f2bb3200dbecd9ecb58
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06576637B1
Reaction notes
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