Dicyclohexylcarbodiimide → S-4-nitrophenyl 3-(4-piperidinopiperidinocarbonyl)propanethioate

HRID 377268

반응식

HRID 377268 반응식
[N:1]1([CH:7]2[CH2:12][CH2:11][N:10]([C:13]([CH2:15][CH2:16][C:17]([OH:19])=O)=[O:14])[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1CCC(N=C=NC2CCCCC2)CC1.[N+:35]([C:38]1[CH:43]=[CH:42][C:41]([SH:44])=[CH:40][CH:39]=1)([O-:37])=[O:36]>C(Cl)Cl>[N:1]1([CH:7]2[CH2:8][CH2:9][N:10]([C:13]([CH2:15][CH2:16][C:17](=[O:19])[S:44][C:41]3[CH:42]=[CH:43][C:38]([N+:35]([O-:37])=[O:36])=[CH:39][CH:40]=3)=[O:14])[CH2:11][CH2:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 158094-NitrobenzenethiolHCID 193585713-(4-Piperidinopiperidinocarbonyl)propionic acid

생성물 1

HCID 19358562S-4-nitrophenyl 3-(4-piperidinopiperidinocarbonyl)propanethioate수율 50%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
4 °C

실험 절차

3-(4-Piperidinopiperidinocarbonyl)propionic acid (0.26 g, 0.97 mmol) and DCC (0.25 g, 1.2 mmol) were dissolved in methylene chloride, followed by the addition of 4-nitrothiophenol (0.23 g, 1.2 mmol). The resulting mixture was stirred for 16 hours at 4° C. and then overnight at room temperature. The reaction mixture was filtered. After the filtrate was concentrated, the residue was purified by chromatography on a silica gel column (chloroform-acetone mixed solvent [10:1→5:1], whereby S-4-nitrophenyl 3-(4-piperidinopiperidinocarbonyl)propanethioate (196 mg, 50%) was obtained.

후처리

  1. customovernight
  2. customat room temperature
  3. filtrationThe reaction mixture was filtered
  4. concentrationAfter the filtrate was concentrated
  5. customthe residue was purified by chromatography on a silica gel column (chloroform-acetone mixed solvent [10:1→5:1]

출처 및 근거

ORD 기록
ord-5ce64b2a2e1e4319b7bcae2833b588f1
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06025385

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