L-Phenylalanine → (3s)-3-Amino-2-hydroxy-4-phenylbutanoic acid

HRID 342908

Reaktionsgleichung

Reaktionsgleichung von HRID 342908
[NH2:1][C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1(=O)[O:18][C:16](=[O:17])C2=CC=CC=C12.C1(C[C@H](N2C(=O)C3=CC=CC=C3C2=O)C(O)=O)C=CC=CC=1.C1(C[C@H](N2C(=O)C3=CC=CC=C3C2=O)C(Cl)=O)C=CC=CC=1.C1(C[C@H](N2C(=O)C3=CC=CC=C3C2=O)C=O)C=CC=CC=1.C(C(O)[C@@H](N1C(=O)C2=CC=CC=C2C1=O)CC1C=CC=CC=1)#N>>[NH2:1][C@@H:2]([CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH:10]([OH:12])[C:16]([OH:18])=[O:17]

Komponenten

7

Edukt 6

HCID 6140L-PhenylalanineHCID 6811Phthalic AnhydrideHCID 334207(2S)-2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-3-phenylpropanoic acidHCID 105671973-phenyl-2(S)-phthalimidopropionyl chlorideHCID 110658013-Phenyl-2(S)-phthalimidopropan-1-alHCID 152893691-cyano-3-phenyl-2(S)-phthalimidopropan-1-ol

Produkt 1

HCID 10856377(3s)-3-Amino-2-hydroxy-4-phenylbutanoic acid

Versuchsvorschrift

L-phenylalanine of the formula ##STR2## is reacted with phthalic anhydride, b) the resultant 3-phenyl-2(S)-phthalimidopropionic acid of the formula ##STR3## is converted into the corresponding acid chloride, c) the resultant 3-phenyl-2(S)-phthalimidopropionic acid chloride of the formula ##STR4## is reduced, d) the resultant 3-phenyl-2(S)-phthalimidopropan-1-al of the formula ##STR5## is transformed into the 1-cyano-3-phenyl-2(S)-phthalimidopropan-1-ol of the formula ##STR6## e) the resultant nitrile of the formula VI is hydrolysed, f) the 3(S)-amino-2-hydroxy-4-phenylbutyric acid formed of the formula ##STR7## is reacted with a low alkyl ester or the phenyl or benzyl ester of chloroformic acid,

Quellen und Nachweise

ORD-Eintrag
ord-6b9f43ca2ed44bd786c5520f96380fce
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859248

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