Potassium Iodide → HCID 67530603, compound

HRID 2388250Notes

Reaction equation

HRID 2388250 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([CH2:11][CH3:12])[C:7]=1[CH2:13]Br)=[O:5])[CH3:2].[CH2:15]([O:17][C:18](=[O:32])[CH2:19][NH:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=1[O:30][CH3:31])[CH3:16].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[CH3:31][O:30][C:23]1[CH:24]=[C:25]([O:28][CH3:29])[CH:26]=[CH:27][C:22]=1[CH2:21][N:20]([CH2:13][C:7]1[C:8]([CH2:11][CH3:12])=[N:9][O:10][C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:19][C:18]([O:17][CH2:15][CH3:16])=[O:32]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 19895532Ethyl 2-(2,4-dimethoxybenzylamino)acetateHCID 67530800HCID 67530800, compound

Product 1

HCID 67530603HCID 67530603, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Bromomethyl-3-ethyl-isoxazole-5-carboxylic acid ethyl ester (1.03 g, 3.93 mmol) was dissolved in 40 mL of acetonitrile. N-(2,4-dimethoxybenzyl)glycine ethyl ester (1.09 g, 4.32 mmol), potassium carbonate (1.63 g, 11.8 mmol) and potassium iodide (0.98 g, 5.90 mmol) were added, and the mixture was stirred at room temperature for 16 h. The solvent was removed in vacuo and the residue was partitioned between CH2Cl2 and water. The aqueous layer was extracted with additional CH2Cl2 and the combined organic layer was dried over MgSO4 and concentrated. The crude oil was purified by flash chromatography (0-30% EtOAc/hexanes) to give 0.88 g of the title compound. MS: (+) m/z 435.53 (M+1).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between CH2Cl2 and water
  3. extractionThe aqueous layer was extracted with additional CH2Cl2
  4. dry with materialthe combined organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe crude oil was purified by flash chromatography (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-13de6047a7464157939151fb7596b032
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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