Tosylmethyl isocyanide → N-Methyl-5-oxazol-5-yl-N-propyl-isophthalamic acid

HRID 732496ノート

反応式

HRID 732496 の反応式
C([O:3][C:4](=[O:20])[C:5]1[CH:17]=[C:16]([CH:18]=[O:19])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)C.S([CH2:31][N+:32]#[C-:33])(C1C=CC(C)=CC=1)(=O)=O.C[O-].[Na+]>CO>[CH3:14][N:10]([CH2:11][CH2:12][CH3:13])[C:8](=[O:9])[C:7]1[CH:6]=[C:5]([CH:17]=[C:16]([C:18]2[O:19][CH:33]=[N:32][CH:31]=2)[CH:15]=1)[C:4]([OH:3])=[O:20]

参加物

5

反応物 3

HCID 161915Tosylmethyl isocyanideHCID 10942334Sodium MethoxideHCID 86615013HCID 86615013、化合物

生成物 1

HCID 68814628N-Methyl-5-oxazol-5-yl-N-propyl-isophthalamic acid収率 65.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Heat a solution of 5-formyl-N-methyl-N-propyl-isophthalamic acid ethyl ester (300 mg, 1.08 mmol), tosylmethyl isocyanide (254 mg, 1.3 mmol), and sodium methoxide (193 mg, 3.57 mmol) in methanol (3.1 mL) at 40° C. for 1 h. Add water to the hot solution and extract with dichloromethane and ethyl acetate. Acidify the aqueous with 5 N HCl, extract with dichloromethane, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 0:100 to 4:96 methanol:dichloromethane) to give the title compound (203 mg, 65%).

後処理

  1. extractionAdd water to the hot solution and extract with dichloromethane and ethyl acetate
  2. extractionextract with dichloromethane
  3. dry with materialdry (magnesium sulfate)
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 0:100 to 4:96 methanol:dichloromethane)

出典と根拠

ORDレコード
ord-a7e7ab1177ad47bfbcd845c2009dd022
出典データセット
uspto-grants-2009_09
特許番号
US07585885B2

反応ノート

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