4-Toluenesulfonyl chloride → HCID 178465150、化合物

HRID 1395821ノート

反応式

HRID 1395821 の反応式
[CH3:1][O:2][C:3](=[O:78])[C@H:4]([CH2:76]O)[NH:5][C:6](=[O:75])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:74])[C@H:13]([CH2:68][C:69]1[N:73]=[CH:72][NH:71][CH:70]=1)[NH:14][C:15](=[O:67])[C@H:16]([C@H:63]([CH2:65][CH3:66])[CH3:64])[NH:17][C:18](=[O:62])[C@H:19]([CH2:54][C:55]1[CH:60]=[CH:59][C:58]([OH:61])=[CH:57][CH:56]=1)[NH:20][C:21](=[O:53])[C@H:22]([CH:50]([CH3:52])[CH3:51])[NH:23][C:24](=[O:49])[C@H:25]([CH2:42][CH2:43][CH2:44][NH:45][C:46](=[NH:48])[NH2:47])[N:26]([C:30](=[O:41])[CH2:31][N:32]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH3:33])[N+:27]([O-:29])=[O:28].S(Cl)(C1C=CC(C)=CC=1)(=O)=O>N1C=CC=CC=1.C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:78])[C:4](=[CH2:76])[NH:5][C:6](=[O:75])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:74])[C@H:13]([CH2:68][C:69]1[N:73]=[CH:72][NH:71][CH:70]=1)[NH:14][C:15](=[O:67])[C@H:16]([C@H:63]([CH2:65][CH3:66])[CH3:64])[NH:17][C:18](=[O:62])[C@H:19]([CH2:54][C:55]1[CH:56]=[CH:57][C:58]([OH:61])=[CH:59][CH:60]=1)[NH:20][C:21](=[O:53])[C@H:22]([CH:50]([CH3:51])[CH3:52])[NH:23][C:24](=[O:49])[C@H:25]([CH2:42][CH2:43][CH2:44][NH:45][C:46](=[NH:47])[NH2:48])[N:26]([C:30](=[O:41])[CH2:31][N:32]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH3:33])[N+:27]([O-:29])=[O:28]

参加物

5

反応物 2

HCID 73974-Toluenesulfonyl chloride2 回HCID 178455908HCID 178455908、化合物

生成物 1

HCID 178465150HCID 178465150、化合物

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8471Triethylamine溶媒

実験手順

3.0 g of t-butoxycarbonylsarcosylnitroarginylvalyltyrosylisoleucylhistidylprolylserine methyl ester is dissolved in 20 ml of pyridine and 10 ml of triethylamine. The solution is cooled in an ice bath. 0.51 g of tosyl chloride is added to the solution. At ten minute intervals, three additional 0.51 g batches of tosyl chloride are added. After standing for two hours, the reaction mixture is filtered. 200 ml of methylene chloride is added to the reaction. The solution is extracted three times with 5% ammonium hydroxide in water. The solution is then dried over sodium sulfate and stripped under vacuum. The residue istaken up in 2% methanol/methylene chloride and passed through a silica gel column to remove the colored impurities and afford the pure product t-butoxycarbonylsarcosylnitroarginylvalyltyrosylisoleucylhistidylprolyldehydroalanine methyl ester.

後処理

  1. temperatureThe solution is cooled in an ice bath
  2. filtrationthe reaction mixture is filtered
  3. addition200 ml of methylene chloride is added to the reaction
  4. extractionThe solution is extracted three times with 5% ammonium hydroxide in water
  5. dry with materialThe solution is then dried over sodium sulfate
  6. customto remove the colored impurities

出典と根拠

ORDレコード
ord-757bed4dfed84fc29ba6867a17f539d4
出典データセット
uspto-grants-1980_05
特許番号
US04204991

反応ノート

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