Triethylamine → HCID 18429271, compound

HRID 1280186Notes

Reaction equation

HRID 1280186 reaction equation
C([O:4][CH:5]([CH2:26][O:27]C(=O)C)[C:6]([NH:8][C:9]1[C:10]([I:25])=[C:11]([CH2:20][O:21]C(=O)C)[C:12]([I:19])=[C:13]([C:17]=1[I:18])[C:14](Cl)=[O:15])=[O:7])(=O)C.[OH:31][CH:32]([CH2:35][OH:36])[CH2:33][NH2:34].[Br-].[Li+].C(N(CC)CC)C>O1CCCC1>[OH:4][CH:5]([CH2:26][OH:27])[C:6]([NH:8][C:9]1[C:10]([I:25])=[C:11]([CH2:20][OH:21])[C:12]([I:19])=[C:13]([C:17]=1[I:18])[C:14]([NH:34][CH2:33][CH:32]([OH:31])[CH2:35][OH:36])=[O:15])=[O:7]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 735613-Amino-1,2-propanediolHCID 82050Lithium BromideHCID 18429133HCID 18429133, compound

Product 1

HCID 18429271HCID 18429271, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

5-[N-(2,3-Diacetoxypropionyl)amino]-3-acetoxymethyl-2,4,6-triiodobenzoyl chloride (7.71 g, 9.9 mmol), 2,3-dihydroxypropylamine (1.48 g, 16.2 mmol), lithium bromide (90 mg, 1 mmol) and triethylamine (2.27 ml, 16.2 mmol) were mixed in tetrahydro-furan (55 ml) at ambient temperature. The temperature was increased to 65° C. and held there for 26 h with efficient stirring, and the mixture was then evaporated to dryness. The residue was dissolved in a mixture of water and methanol (6:1, 70 ml) and treated with a strongly basic anion exchange resin (Dowex 1×8) for 2.5 h. The resin was filtered off, the solution diluted with further water (50 ml) and treated with a strongly acidic cation exchange resin (Amberlyst 15) to bring the pH of the solution to 5.5-6.0. The resin was filtered off and the solution was treated with activated charcoal (0.35 g), filtered and evaporated to a light yellow to white solid residue. This was triturated with acetonitrile (20 ml) for 12 h, giving 5.8 g (70%) of a white crystalline residue.

Workup

  1. customthe mixture was then evaporated to dryness
  2. dissolutionThe residue was dissolved in a mixture of water and methanol (6:1, 70 ml)
  3. additiontreated with a strongly basic anion exchange resin (Dowex 1×8) for 2.5 h
  4. filtrationThe resin was filtered off
  5. additionthe solution diluted with further water (50 ml)
  6. additiontreated with a strongly acidic cation exchange resin (Amberlyst 15)
  7. filtrationThe resin was filtered off
  8. additionthe solution was treated with activated charcoal (0.35 g)
  9. filtrationfiltered
  10. customevaporated to a light yellow to white solid residue
  11. customThis was triturated with acetonitrile (20 ml) for 12 h

Sources & evidence

ORD record
ord-6cc4407f546f4fc88371b96c60fe20c2
Source dataset
uspto-grants-2002_09
Patent number
US06448442B1

Reaction notes

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