HCID 21715954, compound → HCID 86755326, compound

HRID 1004526Notes

Reaction equation

HRID 1004526 reaction equation
CC(C)C[O:4][C:5](=[O:16])[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1.[C:18]([CH2:21][NH:22][C:23]1[C:24]([I:39])=[C:25]([C:29]([I:38])=[C:30]([NH:33][CH2:34][C:35](=[O:37])[CH3:36])[C:31]=1[I:32])[C:26](Cl)=[O:27])(=[O:20])[CH3:19]>CC(N(C)C)=O>[C:35]([CH2:34][NH:33][C:30]1[C:29]([I:38])=[C:25]([C:26]([NH:15][C:12]2[CH:11]=[CH:10][C:9]([CH2:8][CH2:7][CH2:6][C:5]([OH:4])=[O:16])=[CH:14][CH:13]=2)=[O:27])[C:24]([I:39])=[C:23]([NH:22][CH2:21][C:18](=[O:20])[CH3:19])[C:31]=1[I:32])(=[O:37])[CH3:36]

Participants

4

Reactant 2

HCID 21715954HCID 21715954, compoundHCID 53982003HCID 53982003, compound

Product 1

HCID 86755326HCID 86755326, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
92.5 °C

Procedure

To a solution of 4-aminobenzenebutyric acid 2,2-dimethylethyl ester IXb (2.0 g, 7.5 mmol) in dimethylacetamide (DMA 25 mL), was added 3,5 bis(acetylmethylamino)-2,4,6 triiodobenzoyl chloride X (1.98 g, 3 mmol), and the mixture stirred at 90-95° C. for 6 h. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate (200 mL). The organic extract was washed with saturated sodium bicarbonate (250 mL), water and saturated sodium chloride and dried over sodium sulfate. The solvent was removed in vacuum and the residue purified by a silica gel column (150 g) using hexane/EtOAc to obtain the title compound XIb (1.98 g, yield 74%). (MS: m/e 858 (M-H)-.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (200 mL)
  3. extractionThe organic extract
  4. washwas washed with saturated sodium bicarbonate (250 mL), water and saturated sodium chloride
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed in vacuum
  7. customthe residue purified by a silica gel column (150 g)

Sources & evidence

ORD record
ord-9401cf15dfab4a9aabb19f3ea8c8fe00
Source dataset
uspto-grants-2000_04
Patent number
US06051210

Reaction notes

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