Sodium Chloride → 2-(3,4-dichlorophenyl)-2-hydroxy-N-[trans-2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-cyclohexyl]-acetamide

HRID 1375227노트

반응식

HRID 1375227 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:28])[C:10]([NH:12][C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]2[C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([O:26][CH3:27])[CH:20]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].S(C1C=CC(C)=CC=1)(O[C:33]#[C:34][CH3:35])(=O)=O.C[O-].[Na+].[Cl-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:28])[C:10]([NH:12][C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]2[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:35][C:34]#[CH:33])=[C:21]([O:26][CH3:27])[CH:20]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

참가 물질

6

반응물 4

HCID 5234Sodium ChlorideHCID 3715371-Propynyl 4-methylbenzenesulfonateHCID 10942334Sodium MethoxideHCID 115390922-(3,4-dichlorophenyl)-2-hydroxy-N-[trans-2-(4-hydroxy-3-methoxy-phenyl)-cyclohexyl]-acetamide

생성물 1

HCID 116698222-(3,4-dichlorophenyl)-2-hydroxy-N-[trans-2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-cyclohexyl]-acetamide

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 0.6 g (1.4 mmol) of 2-(3,4-dichlorophenyl)-2-hydroxy-N-[trans-2-(4-hydroxy-3-methoxy-phenyl)-cyclohexyl]-acetamide and 0.4 g (1.9 mmol) of propynyl tosylate and 2.7 ml of 1 M solution of sodium methoxide in 10 ml methanol is heated to reflux for 3 hours. The reaction mixture is cooled and poured into 30 ml of aqueous saturated sodium chloride solution and finally extracted with two 100 ml portions of ethyl acetate. The combined organic extract is concentrated under reduced pressure to a residue, which is subjected to column chromatography on silica gel, with 1:1 ethyl acetate/isohexane as the eluant to obtain 2-(3,4-dichlorophenyl)-2-hydroxy-N-[trans-2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-cyclohexyl]-acetamide.

후처리

  1. temperatureto reflux for 3 hours
  2. temperatureThe reaction mixture is cooled
  3. extractionfinally extracted with two 100 ml portions of ethyl acetate
  4. extractionThe combined organic extract
  5. concentrationis concentrated under reduced pressure to a residue, which

출처 및 근거

ORD 기록
ord-f0a44a4d6bff4268a68ed109467666ef
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07166746B2

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