Benzene → trans-1-Methyl-3-diethylamino-4-phenyl-2-azetidinone

HRID 1199182ノート

反応式

HRID 1199182 の反応式
C(O[C:4](=[O:11])[CH2:5][N:6]([CH2:9][CH3:10])[CH2:7][CH3:8])C.[CH:12](=CN)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[NH4+:22].[CH:23]1C=CC=CC=1>C(OCC)C>[CH3:23][N:22]1[C@@H:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@H:5]([N:6]([CH2:7][CH3:8])[CH2:9][CH3:10])[C:4]1=[O:11]

参加物

6

反応物 4

HCID 241BenzeneHCID 25517Ammonium ChlorideHCID 75843Glycine, N,N-diethyl-, ethyl esterHCID 155076Ethenamine, 2-phenyl-

生成物 1

HCID 14262160trans-1-Methyl-3-diethylamino-4-phenyl-2-azetidinone収率 95%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

2.95 g (10 mmoles) of the ethylzinc enolate lithium chloride complex of N,N-diethylglycine ethyl ester (the product obtained from example I) was dissolved in 20 ml benzene at room temperature. To this clear colourless solution was added 1.19 g (10 mmoles) of N-(benzylidene)methylamine. The resulting solution was refluxed for 30 min. During this period some precipitate formed. The reaction mixture was cooled to room temperature and diluted with 25 ml diethyl ether. To this mixture, 10 ml of a saturated aqueous ammonium-chloride solution was added. The aqueous layer was separated and the organic layer was twice washed with 10 ml of an aqueous ammonium chloride solution and twice with 10 ml portions of water, dried over sodium sulfate and concentrated in vacuo yielding 2.2 g (95%) of the 2-azetidinone product as a white solid with the properties: m.p. 70°-71° C. 1H NMR (60 MHz, CDCl3): δ7.30 (m, 5H, arom.), 4.60 (d, J=1.6 Hz, 1H, NCHCHPh), 4.10 (d, J=1.6 Hz, 1H, NCHCHPh), 2.90 (s, 3H, NCH3), 2.90 (q, 4H, NCH2CH3), 1.15 (t, 6H, NCH2CH3).

後処理

  1. temperatureThe resulting solution was refluxed for 30 min
  2. customDuring this period some precipitate formed
  3. customThe aqueous layer was separated
  4. washthe organic layer was twice washed with 10 ml of an aqueous ammonium chloride solution and twice with 10 ml portions of water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-230bca7aec914bceacdf0b22d937f7a7
出典データセット
uspto-grants-1990_02
特許番号
US04898955

反応ノート

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