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

HRID 1075843

反応式

HRID 1075843 の反応式
[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

参加物

4

反応物 2

HCID 11776TriphenylphosphineHCID 21540959N-cyclopropanecarbonyl-5-bromovaleramide

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2605b9d00f7a4c6fbc91d8d4a3bbd40f
出典データセット
uspto-grants-1976_05
特許番号
US03954741

関連ノート

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