4-Toluenesulfonyl chloride → HCID 178465150, 화합물

HRID 1395821노트

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HRID 1395821 반응식
[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]

참가 물질

5

반응물 2

HCID 73974-Toluenesulfonyl chloride2회HCID 178455908HCID 178455908, 화합물

생성물 1

HCID 178465150HCID 178465150, 화합물

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-757bed4dfed84fc29ba6867a17f539d4
출처 데이터셋
uspto-grants-1980_05
특허 번호
US04204991

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