Hydrochloric Acid → (2R,4S,5S)-5-amino-4-hydroxy-2-methyl-6-phenylhexanoic acid (3,3-dimethylbutyl)-amide

HRID 1612428Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1612428
C(OC(=O)[NH:7][C@@H:8]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C@@H:9]([OH:22])[CH2:10][C@H:11]([C:13](=[O:21])[NH:14][CH2:15][CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:12])(C)(C)C.Cl>O1CCOCC1>[CH3:19][C:17]([CH3:18])([CH3:20])[CH2:16][CH2:15][NH:14][C:13](=[O:21])[C@H:11]([CH3:12])[CH2:10][C@H:9]([OH:22])[C@@H:8]([NH2:7])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 69507916[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-carbamic acid t-butyl ester

Produkt 1

HCID 68890142(2R,4S,5S)-5-amino-4-hydroxy-2-methyl-6-phenylhexanoic acid (3,3-dimethylbutyl)-amideAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-carbamic acid t-butyl ester (D1) (264 mg, 0.63 mmol) was treated with 4M HCl in dioxane (5 ml) and the resulting solution was stirred at room temperature for 1 h. It was then evaporated to dryness and the residue was partitioned between satd. aq. sodium carbonate and ethyl acetate. The aqueous layer was separated and extracted with further ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, filtered and evaporated to afford product (179 mg, 89%).

Aufarbeitung

  1. customIt was then evaporated to dryness
  2. customthe residue was partitioned between satd
  3. customThe aqueous layer was separated
  4. extractionextracted with further ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ed53054bab33447c8516de23ebd44c47
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06992103B2

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