HuagongsheHuagongshe Chemistry Print Report · For research reference only
L-Phenylalanine → (3s)-3-Amino-2-hydroxy-4-phenylbutanoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | L-Phenylalanine | HCID 6140 | — |
| Reactant | Phthalic Anhydride | HCID 6811 | — |
| Reactant | (2S)-2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-3-phenylpropanoic acid | HCID 334207 | — |
| Reactant | 3-phenyl-2(S)-phthalimidopropionyl chloride | HCID 10567197 | — |
| Reactant | 3-Phenyl-2(S)-phthalimidopropan-1-al | HCID 11065801 | — |
| Reactant | 1-cyano-3-phenyl-2(S)-phthalimidopropan-1-ol | HCID 15289369 | — |
| Product | (3s)-3-Amino-2-hydroxy-4-phenylbutanoic acid | HCID 10856377 | — |
Reaction Steps
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,
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05859248 |
| Source dataset | uspto-grants-1999_01 |
| ORD ID | ord-6b9f43ca2ed44bd786c5520f96380fce |
| Source note | uspto-grants-1999_01 |