Triphenylphosphine → HCID 21541001, 화합물

HRID 1075844노트

반응식

HRID 1075844 반응식
[CH3:1][C:2]([CH3:14])([CH3:13])[C:3]([NH:5][C:6](=[O:12])[CH2:7][CH2:8][CH2:9][CH2:10][Br:11])=[O:4].[C:15]1([P:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(#N)C>[Br-:11].[CH3:1][C:2]([CH3:14])([CH3:13])[C:3]([NH:5][C:6]([CH2:7][CH2:8][CH2:9][CH2:10][P+:21]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])=[O:4]

참가 물질

4

반응물 2

HCID 11776TriphenylphosphineHCID 21540995HCID 21540995, 화합물

생성물 1

HCID 21541001HCID 21541001, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of 1.82 g. (6.80 mmoles) of the N-trimethylacetyl-5-bromovaleramide prepared above and 2.67 g. (10.2 mmoles) of triphenylphosphine in 18 ml. of acetonitrile was heated to reflux under nitrogen for 96 hours. The solution was concentrated and the resultant solid was triturated with benzene (4x). The triturated solid was purified by silica gel column chromatography using first ethyl acetate to remove high Rf impurities then with a 9:1 mixture of methylene chloride:methanol. The salt, [4-trimethylacetylaminocarbonylbutyl]triphenylphosphonium bromide, was obtained as crystals from methylene chloride:ethyl acetate weighing 0.750 g. melting at 133.5°-138°.

후처리

  1. temperatureto reflux under nitrogen for 96 hours
  2. concentrationThe solution was concentrated
  3. customthe resultant solid was triturated with benzene (4x)
  4. customThe triturated solid was purified by silica gel column chromatography
  5. customto remove high Rf impurities
  6. additionwith a 9:1 mixture of methylene chloride

출처 및 근거

ORD 기록
ord-64c9def88db5419ea21dc114c5ab8788
출처 데이터셋
uspto-grants-1976_05
특허 번호
US03954741

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