Hydrochloric Acid → 3,3-Diphenylalanine

HRID 551295

Reaktionsgleichung

Reaktionsgleichung von HRID 551295
C[O:2][C:3](=[O:26])[CH:4]([NH:18]C(OC(C)(C)C)=O)[CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl>>[NH2:18][CH:4]([CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:26])=[O:2]

Komponenten

3

Edukt 2

HCID 313Hydrochloric AcidHCID 67199473N-[(1,1-Dimethylethoxy)carbonyl]-β-phenylphenylalanine methyl ester

Produkt 1

HCID 2249693,3-Diphenylalanine

Versuchsvorschrift

Reaction was carried out in a similar manner to Example 26, except that 2.5 g of N-Boc-glycine methyl ester was used in place of 1-dimethylethyl-(2R)-(2,6-dichlorophenyl)-5-oxo-3-((1′R)-phenylethyl)tetrahydro-1H-1-imidazolecarboxylate to obtain 640 mg of 2-(N-Boc-amino)-3,3-diphenylpropionic acid methyl ester as a colorless oily material (yield: 14%). Further, 354 mg of 2-(N-Boc-amino)-3,3-diphenylpropionic acid methyl ester was mixed with a 6 M solution of aqueous hydrochloric acid, and the mixture was refluxed for 5 hours. Thereafter, the mixture was washed with toluene, and neutralized with a 30% aqueous solution of sodium hydroxide to obtain a white solid of 2-amino-3,3-diphenylpropionic acid. The retention time of the respective isomers was confirmed by using the product.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 5 hours
  2. washThereafter, the mixture was washed with toluene

Quellen und Nachweise

ORD-Eintrag
ord-6ffe0aec60f34ebe96aa6a0315d7ef4b
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947722B2

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