Dimethylformamide → HCID 58746509, compound

HRID 724724Notes

Reaction equation

HRID 724724 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[I:30])[CH2:5][C@H:6]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:7](=O)[NH:8][CH2:9][C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])(=O)C.[NH4+].C[N:37](C)C=O>O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][C@H:6]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:7]2[NH:37][C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][N:8]=2)[CH:27]=[CH:28][C:29]=1[I:30]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 517165Ammonium AcetateHCID 58746572tert-Butyl (1S)-1-(3-bromo-4-iodobenzyl)-2-oxo-2-[(2-oxo-2-phenylethyl)amino]ethylcarbamate

Product 1

HCID 58746509HCID 58746509, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of tert-butyl (1S)-1-(3-bromo-4-iodobenzyl)-2-oxo-2-[(2-oxo-2-phenylethyl)amino]ethylcarbamate (1.20 g, 1.63 mmol), ammonium acetate (6.30 g, 81.7 mmol) and N,N-dimethylformamide (15.1 mL) was microwave irradiated at 120° C. for 30 min. The reaction was diluted with water and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (440 mg, 38%).

Workup

  1. extractionextracted with ethyl acetate three times
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-5103c16af907488b887e133dea37a39a
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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