4-Toluenesulfonyl chloride → HCID 178465150, compound

HRID 1395821Notes

Reaction equation

HRID 1395821 reaction equation
[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]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chloride2×HCID 178455908HCID 178455908, compound

Product 1

HCID 178465150HCID 178465150, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-757bed4dfed84fc29ba6867a17f539d4
Source dataset
uspto-grants-1980_05
Patent number
US04204991

Reaction notes

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