1-Methylimidazole → Argininamide

HRID 2263455Notes

Reaction equation

HRID 2263455 reaction equation
[NH:1](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:2]([C:15]([OH:17])=O)[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:14])[NH:8]OC(C)(C)C.C1(C)C=C(C)C=C(C)C=1S([N:46]1C=NC([N+]([O-])=O)=N1)(=O)=O.CN1C=CN=C1>C(Cl)Cl>[NH2:1][C@H:2]([C:15]([NH2:46])=[O:17])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:14])[NH2:8]

Participants

5

Reactant 3

HCID 13901-MethylimidazoleHCID 7169013-Nitro-1-(2,4,6-trimethylbenzene-1-sulfonyl)-1H-1,2,4-triazoleHCID 178454584HCID 178454584, compound

Product 1

HCID 178512843Argininamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Fmoc-Arg(OtBu)-OH, 1-mesitylenesulfonyl-3-nitro-1,2,4-triazole (MSNT) and N-methylimidazole were dissolved in CH2Cl2, and the solution was stirred for 5 minutes and thereafter placed into the solid-phase synthesis column containing the resin, followed by stirring at room temperature for 3 hours. The resin was thereafter washed with methylene chloride, isopropanol and DMF and dried. The unreacted hydroxyl group on the solid phase was thereafter acetylated using a 20% DMF solution of acetic anhydride for 20 minutes for capping. The resin was washed with DMF and stirred along with a 20% piperidine/DMF solution for 20 minutes to remove the protective Fmoc group, whereby resin-Arg-NH2 was obtained. The product was washed with DMF and dried.

Workup

  1. customplaced into the solid-phase synthesis column
  2. additioncontaining the resin
  3. stirringby stirring at room temperature for 3 hours
  4. washThe resin was thereafter washed with methylene chloride, isopropanol and DMF
  5. customdried
  6. customfor 20 minutes
  7. washThe resin was washed with DMF
  8. stirringstirred along with a 20% piperidine/DMF solution for 20 minutes
  9. customto remove the protective Fmoc group

Sources & evidence

ORD record
ord-f0fbf37c87a6435ca37e8daf56d98dcd
Source dataset
uspto-grants-2010_12
Patent number
US07851618B2

Reaction notes

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