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

HRID 342913Notes

Reaction equation

HRID 342913 reaction equation
N[C@@H](CC1C=CC=CC=1)[C@H](O)CN1[C@H](C(NC(C)(C)C)=O)C[C@H]2[C@H](CCCC2)C1.[NH2:30][C@H:31]([C:39]([OH:41])=O)[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C1(=O)[O:47][C:45](=[O:46])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>>[NH2:30][C@@H:31]([CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[CH:39]([OH:41])[C:45]([OH:47])=[O:46]

Participants

8

Reactant 7

HCID 6140L-PhenylalanineHCID 6811Phthalic AnhydrideHCID 334207(2S)-2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-3-phenylpropanoic acidHCID 9865804(3S,4aS,8aS)-2-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-tert-butyldecahydroisoquinoline-3-carboxamideHCID 105671973-phenyl-2(S)-phthalimidopropionyl chlorideHCID 110658013-Phenyl-2(S)-phthalimidopropan-1-alHCID 152893691-cyano-3-phenyl-2(S)-phthalimidopropan-1-ol

Product 1

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

Procedure

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,

Sources & evidence

ORD record
ord-e0132c6739cc4eadad5dd10113d25142
Source dataset
uspto-grants-1999_01
Patent number
US05859248

Reaction notes

Loading…