Dimethylformamide → {4-[4-(1-Methylimidazol-4-yl)-3-keto-1-butynyl]-2-phenylbenzoyl}-methionine methyl ester

HRID 383101Notes

Reaction equation

HRID 383101 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH2:7][C:8]([OH:10])=O)[N:4]=[CH:3]1.C(Cl)(=O)C(Cl)=O.CN(C=O)C.[CH3:22][O:23][C:24](=[O:47])[C@H:25]([CH2:43][CH2:44][S:45][CH3:46])[NH:26][C:27](=[O:42])[C:28]1[CH:33]=[CH:32][C:31]([C:34]#[CH:35])=[CH:30][C:29]=1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(N(CC)CC)C>C(Cl)Cl.CCOCC.[Cu]I>[CH3:22][O:23][C:24](=[O:47])[C@H:25]([CH2:43][CH2:44][S:45][CH3:46])[NH:26][C:27](=[O:42])[C:28]1[CH:33]=[CH:32][C:31]([C:34]#[C:35][C:8](=[O:10])[CH2:7][C:5]2[N:4]=[CH:3][N:2]([CH3:1])[CH:6]=2)=[CH:30][C:29]=1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

9

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 758101-Methylimidazoleacetic acidHCID 54338681(4-Ethynyl-2-phenylbenzoyl)methionine methyl ester

Product 1

HCID 54398996{4-[4-(1-Methylimidazol-4-yl)-3-keto-1-butynyl]-2-phenylbenzoyl}-methionine methyl ester

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1-methyl-4-imidazoleacetic acid (5 mmol) in methylene chloride at 0° C. is added oxalyl chloride (6 mmol) and DMF (0.05 mmol). After 30 minute, the solvent is evaporated in vacuo. The residue is redissolved in dichloromethane, followed by the addition of the resultant acetylene from Example 47A (5 mmol), triethylamine (10 mmol), and copper(I) iodide (1 mmol). The reaction is stirred at 25° C. until TLC analysis indicates no starting material is left in the reaction mixture. The reaction is diluted with ether, washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue is then purified by column chromatography on silica gel to give the title compound.

Workup

  1. customthe solvent is evaporated in vacuo
  2. dissolutionThe residue is redissolved in dichloromethane
  3. waitis left in the reaction mixture
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is then purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8132904adecc4b6b80465ababebb04bc
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Reaction notes

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