Triethylamine → N-(3,5-diacetamido-2,4,6-triiodobenzoyl)-sarcosine ethyl ester

HRID 365030Notes

Reaction equation

HRID 365030 reaction equation
C(N(CC)CC)C.[C:8]([NH:11][C:12]1[C:13]([I:27])=[C:14]([C:18]([I:26])=[C:19]([NH:22][C:23](=[O:25])[CH3:24])[C:20]=1[I:21])[C:15](Cl)=[O:16])(=[O:10])[CH3:9].Cl.[CH2:29]([O:31][C:32](=[O:36])[CH2:33][NH:34][CH3:35])[CH3:30]>CN(C)C=O>[CH2:29]([O:31][C:32](=[O:36])[CH2:33][N:34]([C:15](=[O:16])[C:14]1[C:13]([I:27])=[C:12]([NH:11][C:8](=[O:10])[CH3:9])[C:20]([I:21])=[C:19]([NH:22][C:23](=[O:25])[CH3:24])[C:18]=1[I:26])[CH3:35])[CH3:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 160896703,5-Diacetamido-2,4,6-triiodobenzoyl chloride

Product 1

HCID 13506882N-(3,5-diacetamido-2,4,6-triiodobenzoyl)-sarcosine ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

840 ml (6.1 Mol) triethylamine is added to a solution of 759 g (1.2 Mol) 3,5-diacetamido-2,4,6-triiodobenzoyl chloride and 276 g (1.8 Mol) sarcosine ethyl ester hydrochloride in 7600 ml N,N-dimethylformamide and stirred for 1 hr. at 60° C. The reaction mixture is cooled to room temperature, the crystallized triethyl ammonium chloride is filtered, washed with N,N-dimethylformamide and reduced under vacuum in a rotary evaporator. The residue is dissolved in 650 ml methanol and added dropwise to 3 l ethyl acetate. The precipitate is crystallized overnight, filtered to a dry state and finally washed with water, 1N hydrochloric acid, cold saturated sodium bicarbonate, water and dried under vacuum at 60° C. Yield: 685 g (80%).

Workup

  1. customat 60° C
  2. filtrationthe crystallized triethyl ammonium chloride is filtered
  3. washwashed with N,N-dimethylformamide
  4. customreduced under vacuum in a rotary evaporator
  5. dissolutionThe residue is dissolved in 650 ml methanol
  6. additionadded dropwise to 3 l ethyl acetate
  7. customThe precipitate is crystallized overnight
  8. filtrationfiltered to a dry state
  9. washfinally washed with water, 1N hydrochloric acid, cold saturated sodium bicarbonate, water
  10. customdried under vacuum at 60° C

Sources & evidence

ORD record
ord-a3c214318ccb41f28e7ab75943bf1af5
Source dataset
uspto-grants-1986_08
Patent number
US04607123

Reaction notes

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