1,2-Dichloroethane → Benzyl 3-(4-(methylthio)phenylamino)-3-oxopropanoate

HRID 1776491ノート

反応式

HRID 1776491 の反応式
[CH3:1][S:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[CH2:10]([O:17][C:18](=[O:23])[CH2:19][C:20](O)=[O:21])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(Cl)CCl>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[CH3:1][S:2][C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:20](=[O:21])[CH2:19][C:18]([O:17][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:23])=[CH:5][CH:4]=1

参加物

7

反応物 3

HCID 111,2-DichloroethaneHCID 660384-(Methylthio)anilineHCID 1816593-(Benzyloxy)-3-oxopropanoic acid

生成物 1

HCID 86679443Benzyl 3-(4-(methylthio)phenylamino)-3-oxopropanoate収率 45.9%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

4-(methylthio)aniline (500 mg, 3.59 mmol), 3-(benzyloxy)-3-oxopropanoic acid (1046 mg, 5.39 mmol), DMAP (527 mg, 4.31 mmol), and EDC (1377 mg, 7.18 mmol) were dissolved in DMF (7 ml). The reaction was stirred at RT for 4 hours. The reaction mixture was diluted with water, and the precipitate was washed with water, dissolved in EtOAc and extracted with HCl 1N, Na2CO3 sat. sol. and brine. The organic phase was dried over Na2SO4 and concentrated under vacuum to give benzyl 3-(4-(methylthio)phenylamino)-3-oxopropanoate (520 mg, 45.9% yield).

後処理

  1. washthe precipitate was washed with water
  2. dissolutiondissolved in EtOAc
  3. extractionextracted with HCl 1N, Na2CO3 sat. sol. and brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-0ea2da153e1248f7884524b53c5a4582
出典データセット
uspto-grants-2016_02
特許番号
US09265768B2

反応ノート

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