Diethylamine → (4-Ethynyl-2-phenylbenzoyl)methionine methyl ester

HRID 325227Notes

Reaction equation

HRID 325227 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C@H:4]([CH2:21][CH2:22][S:23][CH3:24])[NH:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][C:8]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH2:26](NCC)[CH3:27].C[Si](C#C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1(C)C=CC=CC=1.CCOCC.C([O-])(=O)C.C([O-])(=O)C.[Pd+2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I>[CH3:1][O:2][C:3](=[O:25])[C@H:4]([CH2:21][CH2:22][S:23][CH3:24])[NH:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][C:10]([C:26]#[CH:27])=[CH:9][C:8]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

9

Reactant 4

HCID 8021DiethylamineHCID 66111TrimethylsilylacetyleneHCID 2724141Tetrabutylammonium FluorideHCID 20622824(2-Phenyl4bromobenzoyl)-methionine methyl ester

Product 1

HCID 54338681(4-Ethynyl-2-phenylbenzoyl)methionine methyl ester

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 84538Palladium(2+) acetate--triphenylphosphane (1/2/2)CatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (2-phenyl-4-bromobenzoyl)-methionine methyl ester (100 mmol), diethylamine (300 mmol), trimethylsilylacetylene (110 mmol), bis(triphenylphosphine) palladium diacetate (5 mmol) and copper(I) iodide (3 mmol) in toluene is heated at 60° C. until TLC analysis indicates the starting methyl ester has disappeared. The reaction mixture is concentrated in vacuo, redissolved in ether, filtered through silica gel, and concentrated. The residue is then dissolved in THF, and is treated with tetrabutylammonium fluoride (120 mmol). After TLC analysis indicates that no starting material is left, the reaction mixture is diluted with ether, washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue is then purified with column chromatography on silica gel to give the title product.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. dissolutionredissolved in ether
  3. filtrationfiltered through silica gel
  4. concentrationconcentrated
  5. dissolutionThe residue is then dissolved in THF
  6. waitis left
  7. washwashed with water and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue is then purified with column chromatography on silica gel

Sources & evidence

ORD record
ord-b1295a32a5004ca08bcd2230412b11eb
Source dataset
uspto-grants-2001_04
Patent number
US06221865B1

Reaction notes

Loading…