Water → Boc-beta-chloro-ala-oh

HRID 1089998Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1089998
[Cl:1][CH2:2][C@@H:3]([C:5]([OH:7])=[O:6])[NH2:4].C(N(CC)CC)C.[C:15]([O:19][C:20](ON=C(C1C=CC=CC=1)C#N)=[O:21])([CH3:18])([CH3:17])[CH3:16].O>O1CCOCC1>[C:15]([O:19][C:20]([NH:4][C@H:3]([C:5]([OH:7])=[O:6])[CH2:2][Cl:1])=[O:21])([CH3:18])([CH3:17])[CH3:16]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 4397723-chloro-L-alanine

Produkt 1

HCID 7020770Boc-beta-chloro-ala-ohAusbeute 47,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 1.0 g (6.25 mmol) of 3-chloro-L-alanine and 1.3 mL of triethylamine in 50% aqueous 1,4-dioxane were added 1.69 g (6.90 mmol) of 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile with stirring at room temperature. After 2 hours, the reaction mixture was poured into 20 mL of water and extracted twice with ethyl acetate. The organic layer was washed twice with water and then with saturated brine, dried over anhydrous magnesium sulfate and evaporated to give 0.66 g (40.5%) of white solid. Recrystallization from a mixture of ethyl acetate and n-hexane afforded 0.58 g of the pure product (35.6%) melting at 123°-124° C., with decomposition, and having the structural formula: ##STR75## The identity of the product was confirmed by IR and NMR analyses.

Aufarbeitung

  1. extractionextracted twice with ethyl acetate
  2. washThe organic layer was washed twice with water
  3. dry with materialwith saturated brine, dried over anhydrous magnesium sulfate
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f6bbc24950e443c6adcf7f30c9bf226b
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05079366

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