Triethylamine → HCID 86645259, compound

HRID 2188509Notes

Reaction equation

HRID 2188509 reaction equation
[C:1]([N:4]([CH2:36][CH:37]([OH:40])[CH2:38][NH2:39])[C:5]1[C:6]([I:35])=[C:7]([C:24]([NH:26][C:27](C)([CH3:33])C2COCO2)=[O:25])[C:8]([I:23])=[C:9]([C:21]=1[I:22])[C:10]([NH:12][CH2:13][CH:14]1[CH2:18][O:17][C:16]([CH3:20])([CH3:19])[O:15]1)=[O:11])(=[O:3])[CH3:2].[CH2:41](N(CC)CC)C.Cl[C:49]([C:51]1[C:52]([I:78])=[C:53]([NH:70][C:71]([CH2:73][O:74][C:75](=[O:77])[CH3:76])=[O:72])[C:54]([I:69])=[C:55]([C:58](=[O:68])[NH:59][CH2:60][CH:61]2[CH2:65][O:64][C:63]([CH3:67])([CH3:66])[O:62]2)[C:56]=1[I:57])=[O:50].[CH2:79]([O:81][C:82](=[O:84])[CH3:83])C>CN(C=O)C>[C:1]([N:4]([C:5]1[C:6]([I:35])=[C:7]([C:24](=[O:25])[NH:26][CH2:27][CH:33]2[CH2:79][O:81][C:82]([CH3:41])([CH3:83])[O:84]2)[C:8]([I:23])=[C:9]([C:10](=[O:11])[NH:12][CH2:13][CH:14]2[CH2:18][O:17][C:16]([CH3:20])([CH3:19])[O:15]2)[C:21]=1[I:22])[CH2:36][CH:37]([OH:40])[CH2:38][NH:39][C:49]([C:51]1[C:52]([I:78])=[C:53]([NH:70][C:71]([CH2:73][O:74][C:75](=[O:77])[CH3:76])=[O:72])[C:54]([I:69])=[C:55]([C:58](=[O:68])[NH:59][CH2:60][CH:61]2[CH2:65][O:64][C:63]([CH3:67])([CH3:66])[O:62]2)[C:56]=1[I:57])=[O:50])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 59445361Acetic acid {3-chlorocarbonyl-5-[(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-carbamoyl]-2,4,6-triiodo-phenylcarbamoyl}-methyl esterHCID 866452605-[Acetyl-(3-amino-2-hydroxy-propyl)-amino]-N-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-N'-(dimethyl-[1,3]dioxolan-4-ylmethyl)-2,4,6-triiodo-isophthalamide

Product 1

HCID 86645259HCID 86645259, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[Acetyl-(3-amino-2-hydroxy-propyl)-amino]-N-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-N′-(dimethyl-[1,3]dioxolan-4-ylmethyl)-2,4,6-triiodo-isophthalamide (2.0 g, 2 mmol) in DMF (4 mL) were added triethylamine (0.45 g, 4 mmol, 2 eq) followed by acetic acid {3-chlorocarbonyl-5-[(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-carbamoyl]-2,4,6-triiodo-phenylcarbamoyl}-methyl ester (1.85 g, 2 mmol, 1 eq). The reaction mixture was stirred at room temperature overnight under nitrogen. The mixture was diluted with ethylacetate and washed with water. The organics were collected, dried over MgSO4, filtered and evaporated to dryness. The product was purified by silica column chromatography eluting with ethylacetate/MeOH to give acetic acid {3-[3-(acetyl-{3,5-bis-[(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-carbamoyl]-2,4,6-triiodo-phenyl}-amino)-2-hydroxy-propylcarbamoyl]-5-[(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-carbamoyl]-2,4,6-triiodo-phenylcarbamoyl}-methyl ester (725 μmol, Yield=33%).

Workup

  1. washwashed with water
  2. customThe organics were collected
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe product was purified by silica column chromatography
  7. washeluting with ethylacetate/MeOH

Sources & evidence

ORD record
ord-d18b10525eb548bdb5efcffce986273b
Source dataset
uspto-grants-2012_12
Patent number
US08323619B2

Reaction notes

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