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

HRID 877946ノート

反応式

HRID 877946 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4f728e69c9044a8db628f8d54885759a
出典データセット
uspto-grants-2015_03
特許番号
US08987444B2

反応ノート

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