Ethyl Acetate → N-[(2,6-difluorophenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine 2-[(N,N-diethyl)amino]ethyl ester

HRID 844894

反応式

HRID 844894 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]([NH:11][C@H:12]([C:31]([OH:33])=[O:32])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21](=[O:30])[N:22]([CH3:29])[C:23](=[O:28])[N:24]([CH3:27])[C:25]=2[CH3:26])=[CH:16][CH:15]=1)=[O:10].C(=O)([O-])[O-].[K+].[K+].C(O[CH2:44][CH3:45])(=O)C>O>[CH2:9]([N:11]([CH2:44][CH2:45][O:32][C:31](=[O:33])[C@H:12]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[C:21](=[O:30])[N:22]([CH3:29])[C:23](=[O:28])[N:24]([CH3:27])[C:25]=2[CH3:26])=[CH:18][CH:19]=1)[NH:11][C:9]([C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=1[F:8])=[O:10])[CH2:12][CH3:13])[CH3:3]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 69337579CH9Z955RV6

生成物 1

HCID 18736695N-[(2,6-difluorophenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine 2-[(N,N-diethyl)amino]ethyl ester収率 76%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of N-[(2,6-difluorophenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylaianine (1.0 mmol, 460 mg), 2-[(N,N-diethyl)aminolethyl chloride hydrochloride (8.05 mmol, 1.43 g) and potassium carbonate (8.05 mmol, 1.11 g) in ethyl acetate (5 mL) and water (5 mL) was stirred at room termperature overnight. The layers were separated and the aqueous layer was extracted with ethyl acetate (2×40 mL). The combined extracts were washed with brine (50 mL) and dried over anhydrous sodium sulfate. Filtration of the drying agent and concentration of the filtrate gave the crude product which was purified by silica gel chromatography using a Biotage (40m) column to obtain 426 mg (76% yield) of N-[(2,6-difluorophenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine 2-[(N,N-diethyl)amino]ethyl ester as an amorphous white solid. ES-HRMS m/e calcd for C29H34F2N4O5 (M+H) 557.2570, found 557.2575.

後処理

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×40 mL)
  3. washThe combined extracts were washed with brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationFiltration of the drying agent and concentration of the filtrate
  6. customgave the crude product which
  7. customwas purified by silica gel chromatography

出典と根拠

ORDレコード
ord-55b88d1e9450478b9a20d182d49697d0
出典データセット
uspto-grants-2002_04
特許番号
US06380387B1

関連ノート

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