Sodium Hydroxide → Nalpha-[4(S)-tert-Butoxycarbonylamino-3(S)-hydroxy-6-methylheptyl]-L-leucine

HRID 64643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 64643
C[O:2][C:3](=[O:27])[C@H:4]([CH2:23][CH:24]([CH3:26])[CH3:25])[NH:5][CH2:6][CH2:7][C@H:8]([OH:22])[C@@H:9]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][CH:11]([CH3:13])[CH3:12].[OH-].[Na+]>O1CCOCC1.O>[C:18]([O:17][C:15]([NH:14][C@@H:9]([CH2:10][CH:11]([CH3:13])[CH3:12])[C@@H:8]([OH:22])[CH2:7][CH2:6][NH:5][C@H:4]([C:3]([OH:27])=[O:2])[CH2:23][CH:24]([CH3:25])[CH3:26])=[O:16])([CH3:21])([CH3:19])[CH3:20]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 13672671Nalpha-[4(S)-tert-Butoxycarbonylamino-3(S)-hydroxy-6-methylheptyl]-L-leucine methyl ester

Produkt 1

HCID 13672673Nalpha-[4(S)-tert-Butoxycarbonylamino-3(S)-hydroxy-6-methylheptyl]-L-leucineAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

2 (700 mg) was dissolved in dioxane (8 ml), diluted with H2O (8 ml) and treated with four portions (2 ml each) of 1N NaOH (aqueous) over a 1.5 hour period. The aqueous dioxane was removed in vacuo and the white solid residue dissolved in H2O (10 ml). The product was precipitated by acidification with 1N HCl and collected by filtration to give 3 as a fine white powder (560 mg, 83% yield) after drying.

Aufarbeitung

  1. customThe aqueous dioxane was removed in vacuo
  2. dissolutionthe white solid residue dissolved in H2O (10 ml)
  3. customThe product was precipitated by acidification with 1N HCl
  4. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-0360072153b74d609518361aad83fa96
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04609641

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