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

HRID 1436639Notes

Reaction equation

HRID 1436639 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-de32b489b57041e995c4b1c9a723941f
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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