Triethylamine → N-(3,5-dimethylbenzoyl)-2-methyl-3-[4-(3-thienyl)phenyl]alanine methyl ester

HRID 1957027Notes

Reaction equation

HRID 1957027 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)=[CH:9][CH:8]=1)[NH2:5].[CH2:19](N(CC)CC)C.[CH3:26][C:27]1[CH:28]=[C:29]([CH:33]=[C:34]([CH3:36])[CH:35]=1)[C:30](Cl)=[O:31]>O1CCOCC1.CCOCC>[CH3:1][O:2][C:3](=[O:18])[C@:4]([CH3:19])([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)=[CH:9][CH:8]=1)[NH:5][C:30](=[O:31])[C:29]1[CH:28]=[C:27]([CH3:26])[CH:35]=[C:34]([CH3:36])[CH:33]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 810883,5-Dimethylbenzoyl ChlorideHCID 572132553-[4-(3-Thienyl)phenyl]-alanine methyl ester

Product 1

HCID 67674849N-(3,5-dimethylbenzoyl)-2-methyl-3-[4-(3-thienyl)phenyl]alanine methyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A stirred solution of 3-[4-(3-thienyl)phenyl]-alanine methyl ester (650 mg) and triethylamine (1.64 g, 11.8 mmol) in 1,4-dioxane (10 ml) is added 3,5-dimethylbenzoyl chloride (517 mg, 3.07 mmol) at room temperature. The mixture is stirred at room temperature overnight. The reaction mixture is diluted with ether and washed with 1N hydrochloric acid, sat. sodium bicarbonate and water. The organic layer is dried over magnesium sulfate and concentrated in vacuo. The residue is chromatographed on silica with ethyl acetate/hexane (1:2) to give N-(3,5-dimethylbenzoyl)-2-methyl-3-[4-(3-thienyl)phenyl]alanine methyl ester.

Workup

  1. washwashed with 1N hydrochloric acid, sat. sodium bicarbonate and water
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue is chromatographed on silica with ethyl acetate/hexane (1:2)

Sources & evidence

ORD record
ord-95606a5704ec47e59b96bf3c5d9d6a1d
Source dataset
uspto-grants-1998_07
Patent number
US05780498

Reaction notes

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