Potassium Carbonate → (R)-N-(2-(4-Methoxybenzoylamino)-2-phenylethyl]-4-methyl-benzamide

HRID 23955

Reaction equation

HRID 23955 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([C:7](Cl)=[O:8])=[CH:3][CH:2]=1.[CH3:11][O:12][C:13]1[CH:30]=[CH:29][C:16]([C:17]([NH:19][C@H:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:21][NH2:22])=[O:18])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[NH4+]>O.CO.C(Cl)Cl.O1CCOCC1>[CH3:11][O:12][C:13]1[CH:30]=[CH:29][C:16]([C:17]([NH:19][C@H:20]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:21][NH:22][C:7](=[O:8])[C:4]2[CH:5]=[CH:6][C:1]([CH3:10])=[CH:2][CH:3]=2)=[O:18])=[CH:15][CH:14]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 134054-Methylbenzoyl ChlorideHCID 14923Ammonium HydroxideHCID 54421380(R)-2-(4-methoxybenzoylamino)-2-phenylethylamine

Product 1

HCID 54574847(R)-N-(2-(4-Methoxybenzoylamino)-2-phenylethyl]-4-methyl-benzamideYield 73.1%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

(Acylation Method A) p-Toluoyl chloride (0.22 mL, 1.6 mmol) was added via syringe to a 15° C. stirring mixture of (R)-2-(4-methoxybenzoylamino)-2-phenylethylamine (0.40 g, 1.48 mmol), potassium carbonate (0.27 g, 1.9 mmol), 1,4-dioxane (8 mL), and water (4 mL). TLC analysis (80% methylene chloride, 18% methanol, 2% ammonium hydroxide) indicated reaction completion within 1 h. The solution was diluted with water, and the precipitated solid was collected by vacuum filtration. The precipitate was recrystallized from methanol and dried under vacuum at 50° C. overnight to afford the title compound (0.42 g, 72%) as a white solid.

Workup

  1. customreaction completion within 1 h
  2. filtrationthe precipitated solid was collected by vacuum filtration
  3. customThe precipitate was recrystallized from methanol
  4. customdried under vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-60f098dbdc0944e0b996dc0256d89b59
Source dataset
uspto-grants-2005_02
Patent number
US06855715B1

Linked notes

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