Triphenylphosphine → [4-(Cyclopropanecarbonylaminocarbonyl)butyl]triphenylphosphonium bromide

HRID 1075843

반응식

HRID 1075843 반응식
[CH:1]1([C:4]([NH:6][C:7](=[O:13])[CH2:8][CH2:9][CH2:10][CH2:11][Br:12])=[O:5])[CH2:3][CH2:2]1.[C:14]1([P:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(#N)C>[Br-:12].[CH:1]1([C:4]([NH:6][C:7]([CH2:8][CH2:9][CH2:10][CH2:11][P+:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:13])=[O:5])[CH2:3][CH2:2]1

참가 물질

4

반응물 2

HCID 11776TriphenylphosphineHCID 21540959N-cyclopropanecarbonyl-5-bromovaleramide

생성물 1

HCID 21540964[4-(Cyclopropanecarbonylaminocarbonyl)butyl]triphenylphosphonium bromide수율 23.8%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 4.96 g. (20 mmoles) of the N-cyclopropanecarbonyl-5-bromovaleramide prepared above, 7.86 g. (30 mmoles) of triphenylphosphine, and 50 ml. of acetonitrile were heated at reflux temperatures under nitrogen for 112 hours. The mixture was then concentrated and the resultant white foam was purified by column chromatography on Silica gel (Baker 60-200 mesh) using 5% methanol in methylene chloride as eluent. After removal of starting materials and less polar impurities, the desired [4-(cyclopropanecarbonylaminocarbonyl)butyl]triphenylphosphonium bromide was obtained as a white hygroscopic foam weighing 2.42 g. (23.8% yield).

후처리

  1. additionA mixture of 4.96 g
  2. temperatureat reflux temperatures under nitrogen for 112 hours
  3. concentrationThe mixture was then concentrated
  4. customthe resultant white foam was purified by column chromatography on Silica gel (Baker 60-200 mesh)
  5. customAfter removal of starting materials and less polar impurities

출처 및 근거

ORD 기록
ord-2605b9d00f7a4c6fbc91d8d4a3bbd40f
출처 데이터셋
uspto-grants-1976_05
특허 번호
US03954741

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