N-Acetyl-DL-alanine → Nalpha-acetyl-N-(2-hydroxy-4-methoxyphenyl) alaninamide

HRID 1888715Notes

Reaction equation

HRID 1888715 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[OH:11].[C:12]([NH:15][CH:16]([C:18](O)=[O:19])[CH3:17])(=[O:14])[CH3:13].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.C(OCC)(=O)C>[C:12]([NH:15][C@H:16]([C:18]([NH:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[OH:11])=[O:19])[CH3:17])(=[O:14])[CH3:13]

Participants

8

Reactant 5

HCID 7345N-Acetyl-DL-alanineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 122101842-Amino-5-methoxyphenol Hydrochloride

Product 1

HCID 86660905Nalpha-acetyl-N-(2-hydroxy-4-methoxyphenyl) alaninamideYield 9.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-amino-5-methoxyphenol hydrochloride (5.24 g, 29.8 mmol), N-acetyl-D,L-alanine (3.91 g, 29.8 mmol) and 1-hydroxybenzotriazole (4.03 g, 29.8 mmol) in DMF (5 mL) were added triethylamine (4.15 mL, 29.8 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (5.72 g, 29.8 mmol), and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with 1N hydrochloric acid, 10% aqueous potassium carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by basic silica gel column chromatography (ethyl acetate to methanol:ethyl acetate=1:4), and triturated with ethyl acetate to give the title compound (740 mg, yield 9.8%).

Workup

  1. washthe mixture was washed with 1N hydrochloric acid, 10% aqueous potassium carbonate solution and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was purified by basic silica gel column chromatography (ethyl acetate to methanol:ethyl acetate=1:4)
  5. customtriturated with ethyl acetate

Sources & evidence

ORD record
ord-95c503edeeea4957b7bdf76588e45991
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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