Sodium Hydroxide → HCID 57246922, Verbindung

HRID 565247Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 565247
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][N:8]1[C@@H:11]([CH3:12])[C@@H:10]([CH2:13][CH2:14][CH2:15][C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)[C:9]1=[O:21].[OH-:22].[Na+]>O1CCOCC1>[S:17]1[CH:18]=[CH:19][CH:20]=[C:16]1[CH2:15][CH2:14][CH2:13][C@H:10]([C@@H:11]([NH:8][O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[CH3:12])[C:9]([OH:21])=[O:22]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 70237882HCID 70237882, Verbindung

Produkt 1

HCID 57246922HCID 57246922, VerbindungAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

To a solution of (3R,4S)-1-(2-tetrahydropyranyloxy)-3-(3-(thiophene-2-yl)-1-propyl)-4-methylazetidin-2-one (91 mg, 0.295 mmol) in dioxane (1 mL) is added 1 M aqueous sodium hydroxide (0.44 mL). The solution is stirred at 23° C. for 18 h, then extracted with hexanes (10 mL). The aqueous layer is acidified to pH=3 with saturated aqueous sodium bisulfate solution, and is extracted with two 20 mL portions of ethyl acetate. The combined organics are washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to provide (2R,3S)-2-(3-(thiophene-2-yl)-1-propyl)-3-(2-tetrahydropyranyloxyamino)butanoic acid as an oil (91 mg, 94% yield).

Aufarbeitung

  1. extractionextracted with hexanes (10 mL)
  2. extractionis extracted with two 20 mL portions of ethyl acetate
  3. washThe combined organics are washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-063d4d65673845e38409db17c0fdf108
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06172064B2

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