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
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | L-Phenylalanine | HCID 6140 | — |
| Edukt | Phthalic Anhydride | HCID 6811 | — |
| Edukt | (2S)-2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-3-phenylpropanoic acid | HCID 334207 | — |
| Edukt | (3S,4aS,8aS)-2-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-tert-butyldecahydroisoquinoline-3-carboxamide | HCID 9865804 | — |
| Edukt | 3-phenyl-2(S)-phthalimidopropionyl chloride | HCID 10567197 | — |
| Edukt | 3-Phenyl-2(S)-phthalimidopropan-1-al | HCID 11065801 | — |
| Edukt | 1-cyano-3-phenyl-2(S)-phthalimidopropan-1-ol | HCID 15289369 | — |
| Produkt | (3s)-3-Amino-2-hydroxy-4-phenylbutanoic acid | HCID 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
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US05859248 |
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| Quelldatensatz | uspto-grants-1999_01 |
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| ORD ID | ord-e0132c6739cc4eadad5dd10113d25142 |
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| Quellennotiz | uspto-grants-1999_01 |
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