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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 342913Erstellt: 25. Oktober 2026

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

https://huagongshe.com/reaction/342913

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktL-PhenylalanineHCID 6140—
EduktPhthalic AnhydrideHCID 6811—
Edukt(2S)-2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-3-phenylpropanoic acidHCID 334207—
Edukt(3S,4aS,8aS)-2-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-tert-butyldecahydroisoquinoline-3-carboxamideHCID 9865804—
Edukt3-phenyl-2(S)-phthalimidopropionyl chlorideHCID 10567197—
Edukt3-Phenyl-2(S)-phthalimidopropan-1-alHCID 11065801—
Edukt1-cyano-3-phenyl-2(S)-phthalimidopropan-1-olHCID 15289369—
Produkt(3s)-3-Amino-2-hydroxy-4-phenylbutanoic acidHCID 10856377—

Reaktionsschritte

Process for the production of 2-[3-(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N-tert.-butyl-decahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide of the formula ##STR20## characterised in that a) L-phenylalanine of the formula ##STR21## is reacted with phthalic anhydride, b) the resultant 3-phenyl-2(S)-phthalimidopropionic acid of the formula ##STR22## is converted into the corresponding acid chloride, c) the resultant 3-phenyl-2(S)-phthalimidopropionic acid chloride of the formula ##STR23## is reduced, d) the resultant 3-phenyl-2(S)-phthalimidopropan-1-al of the formula ##STR24## is transformed into the 1-cyano-3-phenyl-2(S)-phthalimidopropan-1-ol of the formula ##STR25## e) the resultant nitrile of the formula VI is hydrolysed, f) the unisolated 3(S)-amino-2-hydroxy-4-phenylbutyric acid formed of the formula ##STR26## is reacted with a low alkyl ester or the phenyl or benzyl ester of chloroformic acid,

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS05859248
Quelldatensatzuspto-grants-1999_01
ORD IDord-e0132c6739cc4eadad5dd10113d25142
Quellennotizuspto-grants-1999_01