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

HRID 1776491노트

반응식

HRID 1776491 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0ea2da153e1248f7884524b53c5a4582
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09265768B2

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