Water → N,N'-Bis(2,3-dihydroxypropionyl)-3,5-diamino-2,4,6-triiodobenzylalcohol

HRID 1604153Notes

Reaction equation

HRID 1604153 reaction equation
CC1(C)[O:6][CH:5]([C:7]([NH:9][C:10]2[C:11]([I:33])=[C:12]([C:18]([I:32])=[C:19]([NH:22][C:23]([CH:25]3[CH2:29][O:28]C(C)(C)[O:26]3)=[O:24])[C:20]=2[I:21])[CH2:13]CC([O-])=O)=[O:8])[CH2:4][O:3]1.[OH2:35]>CO.Cl>[OH:26][CH:25]([CH2:29][OH:28])[C:23]([NH:22][C:19]1[C:18]([I:32])=[C:12]([C:11]([I:33])=[C:10]([NH:9][C:7](=[O:8])[CH:5]([OH:6])[CH2:4][OH:3])[C:20]=1[I:21])[CH2:13][OH:35])=[O:24]

Participants

5

Reactant 2

HCID 962WaterHCID 18429246N,N'-Bis(2,2-dimethyl-1,3-dioxolane-4-carbonyl)-3,5-diamino-2,4,6-triiodobenzylacetate

Product 1

HCID 18429330N,N'-Bis(2,3-dihydroxypropionyl)-3,5-diamino-2,4,6-triiodobenzylalcohol

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

N,N'-Bis(2,2-dimethyl-1,3-dioxolane-4-carbonyl)-3,5-diamino-2,4,6-triiodobenzylacetate (1.25 g, 1.55 mol) was dissolved in a mixture of water (50 ml), methanol (25 ml) and concentrated HCl (0.5 ml). After stirring for 4 h, the solution was neutralized with aqueous NaH2PO4 and the solvents were removed by evaporation. The residue was dissolved in water (10 ml) and the pH was adjusted to 12 with aqueous NaOH. After 30 min, the solution was again neutralized and the solvent was evaporated. The product was purified by preparative HPLC. Yield: 483 mg (45%).

Workup

  1. customthe solvents were removed by evaporation
  2. dissolutionThe residue was dissolved in water (10 ml)
  3. waitAfter 30 min
  4. customthe solvent was evaporated
  5. customThe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-b9ca1e106de84bc5be7a32dd904dc836
Source dataset
uspto-grants-1999_11
Patent number
US05993780

Reaction notes

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