Dimethyl Sulfoxide → N-butyl-2-((4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl)acetamide

HRID 877946Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 877946
[CH2:1]([NH:5][C:6](=[O:18])[CH2:7][C@H:8]1[CH2:13][C@@H:12]([CH2:14][OH:15])[O:11][C:10]([CH3:17])([CH3:16])[O:9]1)[CH2:2][CH2:3][CH3:4].C(Cl)(=O)C(Cl)=O.CS(C)=O.C(N(CC)CC)C>C(Cl)Cl.C(O)(=O)C>[CH2:1]([NH:5][C:6](=[O:18])[CH2:7][C@H:8]1[CH2:13][C@@H:12]([CH:14]=[O:15])[O:11][C:10]([CH3:17])([CH3:16])[O:9]1)[CH2:2][CH2:3][CH3:4]

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 53339170N-butyl-2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetamide

Produkt 1

HCID 24826227N-butyl-2-((4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

N-butyl-2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetamide (2 grams) in methylene chloride (10 ml) was added a mixture of oxalyl chloride (1.46 grams), dimethyl sulfoxide (1.36 ml) and methylene chloride (12 ml) at −65 to −60° C. under nitrogen atmosphere and stirred for 45 minutes. Triethylamine (5 ml) was added to the reaction mixture at −65 to −60° C., stirred for 60 minutes and then added to ice-water. The reaction mixture was acidified with acetic acid solution and stirred. Both organic and aqueous layers were separated and organic layer washed with water followed by sodium chloride solution. The solvent from organic layer was distilled off under reduced pressure to get the title compound.

Aufarbeitung

  1. stirringstirred for 60 minutes
  2. stirringstirred
  3. customBoth organic and aqueous layers were separated
  4. washorganic layer washed with water
  5. distillationThe solvent from organic layer was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4f728e69c9044a8db628f8d54885759a
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987444B2

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