Diethylamine → {4-[2-(Imidazol-2-yl)ethynyl]-2-phenylbenzoyl}-methionine methyl ester

HRID 325228

Reaction equation

HRID 325228 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C@H:4]([CH2:22][CH2:23][S:24][CH3:25])[NH:5][C:6](=[O:21])[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[CH:14])=[CH:9][C:8]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Br[C:28]1[N:29]=[CH:30][NH:31][CH:32]=1.C(NCC)C>C1(C)C=CC=CC=1.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:26])[C@H:4]([CH2:22][CH2:23][S:24][CH3:25])[NH:5][C:6](=[O:21])[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:30]2[NH:29][CH:28]=[CH:32][N:31]=2)=[CH:9][C:8]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 8021DiethylamineHCID 54338681(4-Ethynyl-2-phenylbenzoyl)methionine methyl esterHCID 178418934HCID 178418934, compound

Product 1

HCID 69930468{4-[2-(Imidazol-2-yl)ethynyl]-2-phenylbenzoyl}-methionine methyl ester

Reagents, catalysts & solvents 3

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

Procedure

The resultant product from Example 47A (5 mmol) is mixed with 4-bromoimidazole (5 mmol), diethylamine (1 mL), bis(triphenylphosphine) palladium diacetate (0.1 mmol) and copper(I) iodide (0.1 mmol) in toluene. The mixture is stied at 25° C. until TLC analysis indicates the reaction is complete. The reaction mixture is concentrated in vacuo, and the residue is purified with column chromatography on silica gel to give the title product.

Workup

  1. customis stied at 25° C. until TLC analysis
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. customthe residue is purified with column chromatography on silica gel

Sources & evidence

ORD record
ord-5ea27226ef3a42f78a7d8d7d2e59401e
Source dataset
uspto-grants-2001_04
Patent number
US06221865B1

Linked notes

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