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

HRID 732496노트

반응식

HRID 732496 반응식
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]

참가 물질

5

반응물 3

HCID 161915Tosylmethyl isocyanideHCID 10942334Sodium MethoxideHCID 86615013HCID 86615013, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-a7e7ab1177ad47bfbcd845c2009dd022
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585885B2

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