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

HRID 1888715ノート

反応式

HRID 1888715 の反応式
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]

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-95c503edeeea4957b7bdf76588e45991
出典データセット
uspto-grants-2013_08
特許番号
US08501804B2

反応ノート

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