Acetamidomalonic acid diethyl ester → Diethyl 2-acetylamino-2-(2-methoxy-6-nitrobenzyl)malonate

HRID 1828332

反応式

HRID 1828332 の反応式
[Na].[C:2]([NH:5][CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:4])[CH3:3].[CH3:17][O:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[C:20]=1[CH2:21]Br>C(O)C.O1CCCC1>[C:2]([NH:5][C:6]([CH2:21][C:20]1[C:23]([N+:27]([O-:29])=[O:28])=[CH:24][CH:25]=[CH:26][C:19]=1[O:18][CH3:17])([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:4])[CH3:3]

参加物

6

反応物 3

HCID 14041Acetamidomalonic acid diethyl esterHCID 186047Benzene, 2-(bromomethyl)-1-methoxy-3-nitro-HCID 5360545Sodium

生成物 1

HCID 21974615Diethyl 2-acetylamino-2-(2-methoxy-6-nitrobenzyl)malonate収率 80.8%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium metal (1.15 g) was dissolved in absolute ethanol (500 mL), and to the resulting solution was added diethyl 2-acetylaminomalonate (9.1 g). After 15 min at room temperature, a solution of 2-methoxy-6-nitrobenzyl bromide (J. Med. Chem. 1977, 20, 190–196) (8.6 g) in tetrahydrofuran (25 mL) was added over 2 min. After 16 h stirring at room temperature the mixture was evaporated. The residue was dissolved in a mixture of ethyl acetate and water. The ethyl acetate layer was separated and washed sequentially with water and brine before drying over anhydrous sodium sulfate. Evaporation was followed by silica gel chromatography eluting initially with dichloromethane, followed by ethyl acetate, to obtain diethyl 2-acetylamino-2-(2-methoxy-6-nitrobenzyl)malonate (10.8 g).

後処理

  1. customwas evaporated
  2. dissolutionThe residue was dissolved in a mixture of ethyl acetate and water
  3. customThe ethyl acetate layer was separated
  4. washwashed sequentially with water and brine
  5. dry with materialbefore drying over anhydrous sodium sulfate
  6. customEvaporation
  7. washeluting initially with dichloromethane

出典と根拠

ORDレコード
ord-cdf686f2fa4b4b22bee718b4821bab64
出典データセット
uspto-grants-2006_06
特許番号
US07057046B2

関連ノート

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