N,N-dimethylhydroxylamine hydrochloride → 2-[(4R,6S)-6-methanesulfonyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl]-N-methoxy-N-methyl-acetamide

HRID 445932

Reaktionsgleichung

Reaktionsgleichung von HRID 445932
[CH3:1][S:2]([O:5][CH2:6][C@H:7]1[O:12][C:11]([CH3:14])([CH3:13])[O:10][C@@H:9]([CH2:15][C:16]([OH:18])=O)[CH2:8]1)(=[O:4])=[O:3].C([N:26]1[CH:30]=CN=C1)(N1C=CN=C1)=O.Cl.CN(C)O.[C:36](=O)(O)[O-:37].[Na+]>O.C(OCC)(=O)C>[CH3:1][S:2]([O:5][CH2:6][C@H:7]1[O:12][C:11]([CH3:13])([CH3:14])[O:10][C@@H:9]([CH2:15][C:16]([N:26]([O:37][CH3:36])[CH3:30])=[O:18])[CH2:8]1)(=[O:3])=[O:4]

Komponenten

7

Edukt 4

HCID 27969N,N-dimethylhydroxylamine hydrochlorideHCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 22850992[(4R,6S)-6-methanesulfonyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid

Produkt 1

HCID 866815082-[(4R,6S)-6-methanesulfonyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl]-N-methoxy-N-methyl-acetamideAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Ethyl acetate (50.0 mL) was added to [(4R,6S)-6-methanesulfonyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid (10.0 g) prepared in Preparation 8. The reaction mixture was cooled to 0˜5° C. and then 1,1′-carbonyldiimidazole (7.6 g) was slowly added thereto. The temperature of the reaction mixture was raised to 20˜30° C. The reaction mixture was stirred for 3 hours. Dimethylhydroxyamine hydrochloride (5.6 g) and sodium bicarbonate (3.2 g) were added to the reaction mixture, which was then stirred for over 3 hours while maintaining the temperature of 20˜25° C. Water (40.0 mL) was added to the reaction mixture under stirring. The separated organic layer was concentrated under reduced pressure to obtain 2-[(4R,6S)-6-methanesulfonyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl]-N-methoxy-N-methyl-acetamide (10.0 g, yield 87%).

Aufarbeitung

  1. customprepared in Preparation 8
  2. temperatureThe reaction mixture was cooled to 0˜5° C.
  3. temperatureThe temperature of the reaction mixture was raised to 20˜30° C
  4. stirringwas then stirred for over 3 hours
  5. temperaturewhile maintaining the temperature of 20˜25° C
  6. stirringunder stirring
  7. concentrationThe separated organic layer was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ce19986653994d2999385ce1f04a5336
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476432B2

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