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

HRID 11571

반응식

HRID 11571 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f049805b02c647ba9683e13a05b400db
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098235B2

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