2-Nitrophenol → N-(3,5-diacetamido-2,4,6-triiodobenzoyl)-sarcosine-o-nitrophenyl ester

HRID 365035Notes

Reaction equation

HRID 365035 reaction equation
[C:1]([NH:4][C:5]1[C:6]([I:25])=[C:7]([C:16]([I:24])=[C:17]([NH:20][C:21](=[O:23])[CH3:22])[C:18]=1[I:19])[C:8]([N:10]([CH2:12][C:13]([OH:15])=[O:14])[CH3:11])=[O:9])(=[O:3])[CH3:2].[N+:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1O)([O-:28])=[O:27].O1CCCC1>CN(C)C=O>[N+:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[O:14][C:13](=[O:15])[CH2:12][N:10]([C:8](=[O:9])[C:7]1[C:6]([I:25])=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[C:18]([I:19])=[C:17]([NH:20][C:21](=[O:23])[CH3:22])[C:16]=1[I:24])[CH3:11])([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 69472-NitrophenolHCID 8028TetrahydrofuranHCID 20239174HCID 20239174, compound

Product 1

HCID 20239173N-(3,5-diacetamido-2,4,6-triiodobenzoyl)-sarcosine-o-nitrophenyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

6.85 g (10 mMol) N-(3,5-diacetamido-2,4,6-triiodobenzoyl)-sarcosine and 1.7 g (12.2 mMol) o-nitrophenol are dissolved in 15 ml N,N-dimethylformamide. 60 ml tetrahydrofuran is added to this solution which is then cooled down to 0° C. 2,5 g (12 mMol) N,N-dicyclohexylcarbodiimide is added. The reaction runs for 2 hours at 0° C. and overnight at room temperature. The precipitate (N,N'-dicyclohexylurea) is filtered off, washed with 10 ml N,N-dimethylformamide, the tetrahydrofuran is distilled, the solution kept in the refrigerator overnight and then the dicyclohexylurea is again filtered off. The organic solution is added dropwise to 250 ml ether, the precipitate is decantered, dissolved with 25 ml N,N-dimethylformamide and added to water dropwise. The precipitate is filtered, washed with saturated sodium bicarbonate solution and water and dried. Yield: 5.4 g (67%).

Workup

  1. filtrationThe precipitate (N,N'-dicyclohexylurea) is filtered off
  2. washwashed with 10 ml N,N-dimethylformamide
  3. distillationthe tetrahydrofuran is distilled
  4. customkept in the refrigerator overnight
  5. filtrationthe dicyclohexylurea is again filtered off
  6. additionThe organic solution is added dropwise to 250 ml ether
  7. dissolutiondissolved with 25 ml N,N-dimethylformamide
  8. additionadded to water dropwise
  9. filtrationThe precipitate is filtered
  10. washwashed with saturated sodium bicarbonate solution and water
  11. customdried

Sources & evidence

ORD record
ord-8f3ee87c2cf943219e1117f37b3c33bf
Source dataset
uspto-grants-1986_08
Patent number
US04607123

Reaction notes

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