Hydrochloric Acid → N-Acetyl-3-hydroxymethyl-5-(2,3-dihydroxypropylaminocarbonyl)-N-(2,3-dihydroxypropyl)-2,4,6-triiodoaniline

HRID 1418261Notes

Reaction equation

HRID 1418261 reaction equation
[C:1]([NH:4][C:5]1[C:10]([I:11])=[C:9]([C:12]([NH:14][CH2:15][CH:16]([O:22]C(=O)C)[CH2:17][O:18]C(=O)C)=[O:13])[C:8]([I:26])=[C:7]([CH2:27][O:28]C(=O)C)[C:6]=1[I:32])(=[O:3])[CH3:2].[OH-].[Na+].Br[CH2:36][CH:37]([OH:40])[CH2:38][OH:39].Cl>CO.O>[C:1]([N:4]([CH2:36][CH:37]([OH:40])[CH2:38][OH:39])[C:5]1[C:10]([I:11])=[C:9]([C:12]([NH:14][CH2:15][CH:16]([OH:22])[CH2:17][OH:18])=[O:13])[C:8]([I:26])=[C:7]([CH2:27][OH:28])[C:6]=1[I:32])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 208273-Bromo-1,2-propanediol2×HCID 18429152N-acetyl-3-acetoxymethyl-5-(2,3-diacetoxypropylaminocarbonyl)-2,4,6-triiodoaniline

Product 1

HCID 18429229N-Acetyl-3-hydroxymethyl-5-(2,3-dihydroxypropylaminocarbonyl)-N-(2,3-dihydroxypropyl)-2,4,6-triiodoaniline

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

N-acetyl-3-acetoxymethyl-5-(2,3-diacetoxypropylaminocarbonyl)-2,4,6-triiodoaniline (1.0 g, 1.27 mmol) was suspended in a mixture of methanol (6 ml) and water (30 ml) and pH was adjusted to 12.0 using a 2M aqueous solution of NaOH. After stirring for 1 h, 1-bromo-2,3-propanediol (0.99 g, 6.4 mmol) was added and the pH was adjusted to 11.6 using a 2M aqueous solution of HCl. 1-Bromo-2,3-propanediol (0.99 g, 6.4 mmol) was again added after 16 and 18 h and after 24 h, pH was adjusted to 6.5 using a 2M aqueous solution of HCl. After evaporation, the residue was purified by preparative HPLC. Yield: 0.373 g (40%).

Workup

  1. waitafter 24 h
  2. customAfter evaporation
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-dfb9e4f09a9745568db2c18c26553efd
Source dataset
uspto-grants-1999_03
Patent number
US05882628

Reaction notes

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