Hydrochloric Acid → 5-[Acetyl-(3-amino-2-hydroxy-propyl)-amino]-N,N'-bis-(2,3-dihydroxy-propyl)-2,4,6-triiodo-isophthalamide

HRID 2188508Notes

Reaction equation

HRID 2188508 reaction equation
[OH-:1].[K+].[C:3]([NH:6][C:7]1[C:8]([I:31])=[C:9]([C:23]([NH:25][CH2:26][CH:27]([OH:30])[CH2:28][OH:29])=[O:24])[C:10]([I:22])=[C:11]([C:20]=1[I:21])[C:12]([NH:14][CH2:15][CH:16]([OH:19])[CH2:17][OH:18])=[O:13])(=[O:5])[CH3:4].B(O)(O)O.Cl>O.CC(O)(C)C>[C:3]([N:6]([CH2:11][CH:20]([OH:1])[CH2:7][NH2:6])[C:7]1[C:20]([I:21])=[C:11]([C:12]([NH:14][CH2:15][CH:16]([OH:19])[CH2:17][OH:18])=[O:13])[C:10]([I:22])=[C:9]([C:8]=1[I:31])[C:23]([NH:25][CH2:26][CH:27]([OH:30])[CH2:28][OH:29])=[O:24])(=[O:5])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7628Boric AcidHCID 14797Potassium Hydroxide2×HCID 111153265-Acetamido-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide

Product 1

HCID 594811625-[Acetyl-(3-amino-2-hydroxy-propyl)-amino]-N,N'-bis-(2,3-dihydroxy-propyl)-2,4,6-triiodo-isophthalamideYield 19%

Reagents, catalysts & solvents 1

HCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

To a stirred solution of Water/tBuOH (2:1, 8 mL:10 mL) and KOH (0.73 g, 13 mmol, 1.2 eq was added at 40° C. 5-Acetylamino-N,N′-bis-(2,3-dihydroxy-propyl)-2,4,6-triiodo-isophthalamide (8.1 g, 11 mmol). To the clear solution was then added boric acid (0.47 g, 8 mmol, 0.7 eq). The mixture was cooled to room temperature and the pH adjusted to pH 12.6-13.0 with KOH. t-Butyl n-(2-oxiranyl-methyl)carbamate (0.996 g, 8 mmol, 0.7 eq) was added, and the pH was measured several times and adjusted to 12.6-13.0. The mixture was stirred over the weekend. An aqueous solution of HCl was then added until pH 4. The reaction mixture was evaporated to dryness. The product was purified by C18 column chromatography eluting with MeOH/Water to give 5-[Acetyl-(3-amino-2-hydroxy-propyl)-amino]-N,N′-bis-(2,3-dihydroxy-propyl)-2,4,6-triiodo-isophthalamide (2.09 mmol, Yield=19%).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customThe product was purified by C18 column chromatography
  3. washeluting with MeOH/Water

Sources & evidence

ORD record
ord-dc377a2d1b404587bcb6fd3d217c0506
Source dataset
uspto-grants-2012_12
Patent number
US08323619B2

Reaction notes

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