Ethyl Acetate → HCID 18688969, compound

HRID 1734974Notes

Reaction equation

HRID 1734974 reaction equation
[NH2:1][C:2]1[C:3]([I:38])=[C:4]([C:24]([NH:26][CH2:27][CH:28]([O:34]C(=O)C)[CH2:29][O:30]C(=O)C)=[O:25])[C:5]([I:23])=[C:6]([C:21]=1[I:22])[C:7]([NH:9][CH2:10][CH:11]([O:17]C(=O)C)[CH2:12][O:13]C(=O)C)=[O:8].[C:39](Cl)(=[O:62])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48]#[C:49][C:50]#[C:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61].C(OCC)(=O)C>ClCCl>[OH:17][CH:11]([CH2:12][OH:13])[CH2:10][NH:9][C:7](=[O:8])[C:6]1[C:21]([I:22])=[C:2]([NH:1][C:39](=[O:62])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48]#[C:49][C:50]#[C:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])[C:3]([I:38])=[C:4]([C:24]([NH:26][CH2:27][CH:28]([OH:34])[CH2:29][OH:30])=[O:25])[C:5]=1[I:23]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 98975345-Amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide TetraacetateHCID 15186552HCID 15186552, compound

Product 1

HCID 18688969HCID 18688969, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Amino,N,N'-bis(2,3-diacetoxypropyl)-2,4,6-triiodoisophthalamide (2.19 g, 2.5 mmol) and 10,12-tricosadiynoyl chloride (1.82 g, 5 mmol) were dissolved in 20 ml dichloromethane. The solution was stirred for 3 days at ambient temperature under a nitrogen atmosphere. TLC (ethyl acetate) indicated that the reaction was complete. The reaction mixture was evaporated and dissolved in a mixture of methanol (30 ml) and 1M sodium hydroxide solution (15 ml). After 1 hour TLC (methanol/chloroform) indicated that the reaction was complete. The solution was neutralized with concentrated hydrochloric acid. The residue was dissolved in chloroform and filtered. The solvent was removed and the reaction mixture was purified through silica gel with methanol/chloroform (1:3) to give the title compound. 1H NMR (300 MHz, DMSO): δ0.8 (CH3, t), 1.2-1.7 (17×CH2, m), 2.2-2.3 (2×CH2, t), 3.1-3.2 (2×CH2NH, m), 3.3-3.5 (2×CH2OH, m), 3.6-3.8 (2×CHOH), 4.4-4.7 (4×OH, m), 8.4-8.5 (2×CONH, m), 9.8 (2×ArNHCO, s).

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutiondissolved in a mixture of methanol (30 ml) and 1M sodium hydroxide solution (15 ml)
  3. waitAfter 1 hour TLC (methanol/chloroform) indicated that the reaction
  4. dissolutionThe residue was dissolved in chloroform
  5. filtrationfiltered
  6. customThe solvent was removed
  7. customthe reaction mixture was purified through silica gel with methanol/chloroform (1:3)

Sources & evidence

ORD record
ord-4b95c8e92b81488aad30d638270e5033
Source dataset
uspto-grants-1996_07
Patent number
US05536490

Reaction notes

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