Toluene → N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenyl-2-prop-2-ynyloxy-butyramide

HRID 643232노트

반응식

HRID 643232 반응식
[CH2:1](Br)[C:2]#[CH:3].C1(C)C=CC=CC=1.[OH:12][CH:13]([CH:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH3:32])[C:14]([NH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]#[CH:28])=[C:21]([O:29][CH3:30])[CH:20]=1)=[O:15].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[CH3:30][O:29][C:21]1[CH:20]=[C:19]([CH2:18][CH2:17][NH:16][C:14](=[O:15])[CH:13]([O:12][CH2:3][C:2]#[CH:1])[CH:31]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH3:32])[CH:24]=[CH:23][C:22]=1[O:25][CH2:26][C:27]#[CH:28]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 7842Propargyl bromideHCID 14798Sodium HydroxideHCID 592605822-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)ethyl]-3-phenyl-butyramide

생성물 1

HCID 59260581N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenyl-2-prop-2-ynyloxy-butyramide

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 6344Dichloromethane용매

실험 절차

A 80% solution of propargyl bromide in toluene (1.2 g, 7.8 mmol) is added slowly at room temperature to a mixture of 2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)ethyl]-3-phenyl-butyramide (2.4 g, 6.5 mmol), 30% sodium hydroxide solution (6.0 ml, 33 mmol) and catalytic amounts of tetrabutylammonium bromide (50 mg) in 25 ml of dichloromethane. The reaction is stirred for 16 hours at +40° C. Subsequently the mixture is evaporated and the residue is diluted with water and dichloromethane. The phases are separated and the aqueous phase is extracted three times with dichloromethane. The combined organic layer is washed with brine, dried over sodium sulfate and evaporated. The remaining oil is purified by chromatography on silica gel (ethyl acetate/hexane 1:1) to yield N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenyl-2-prop-2-ynyloxy-butyramide (E1.24).

후처리

  1. customSubsequently the mixture is evaporated
  2. additionthe residue is diluted with water and dichloromethane
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted three times with dichloromethane
  5. washThe combined organic layer is washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe remaining oil is purified by chromatography on silica gel (ethyl acetate/hexane 1:1)

출처 및 근거

ORD 기록
ord-ac59e081a59742bdb0f46e650f1a7bd5
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700522B2

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