Ethyl 2-(diphenylmethyleneamino)acetate → HCID 58222080、化合物

HRID 1192364ノート

反応式

HRID 1192364 の反応式
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][N:6]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].CC(C)([O-])C.[K+].Br[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=1[CH3:36]>CS(C)=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:20])[CH:5]([N:6]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=1[CH3:36])[CH3:2]

参加物

6

反応物 3

HCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 23665647Potassium tert-butoxideHCID 53403081Benzene, 1-(bromomethyl)-4-chloro-2-methyl-

生成物 1

HCID 58222080HCID 58222080、化合物収率 50.1%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution containing (Benzhydrylidene-amino)-acetic acid ethyl ester (2.3 g, 8.6 mmol) in 50 mL of DMSO under a nitrogen atmosphere was added potassium t-butoxide (1.2 g, 11 mmol) After stirring for 20 minutes, 1-Bromomethyl-4-chloro-2-methyl-benzene (1.89 g, 8.6 mmol) was added and the reaction allowed to stir at room temperature overnight. The reaction was diluted with ethyl acetate and washed with brine. The organic phase was dried over magnesium sulfate. Filtration, removal of solvent and purification of the residue via biotage eluting with 20% ethyl acetate/hexanes gave 2-(Benzhydrylidene-amino)-3-(4-chloro-2-methyl-phenyl)-propionic acid ethyl ester (1.75 g, 50%) as a yellow oil. LCMS (APCI+) m/z 406 [M+H]+; Rt: 4.16 min.

後処理

  1. stirringto stir at room temperature overnight
  2. washwashed with brine
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationFiltration, removal of solvent and purification of the residue via biotage
  5. washeluting with 20% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-10027a9d26604e77b24978e6302068ff
出典データセット
uspto-grants-2014_03
特許番号
US08680114B2

反応ノート

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