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

HRID 732496Notes

Reaction equation

HRID 732496 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-a7e7ab1177ad47bfbcd845c2009dd022
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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