Trifluoroacetic acid → HCID 178430659, compound

HRID 1936576Notes

Reaction equation

HRID 1936576 reaction equation
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([NH:18][C:19]([NH:31][C:32]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[O:33])=[N:20][C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:22])=[C:16]([CH3:17])[C:11]=2[N:10]=[CH:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:24]([O:23][C:21]([N:20]=[C:19]([NH:31][C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[NH:18][C:15]1[CH:14]=[CH:13][C:12]2[N:8]=[CH:9][NH:10][C:11]=2[C:16]=1[CH3:17])=[O:22])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178430657HCID 178430657, compound

Product 1

HCID 178430659HCID 178430659, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.) solution of 874 mg of 1-(tert-butoxycarbonyl)-5-[N2, N3-bis(benzyloxycarbonyl)guanidino]-4-methylbenzimidazole in 2 mL of methylene chloride is added 2 mL of trifluoroacetic acid. The resulting solution is stirred at room temperature for 30 minutes, then rotary evaporated. The residue is purified by flash column chromatography on silica gel, eluting with 20% methanol/chloroform followed by recrystallization from hexanes/methylene chloride to provide 573 mg of 5-[N2,N3-bis(benzyloxycarbonyl)guanidino]-4-methylbenzimidazole as a white solid.

Workup

  1. customThe residue is purified by flash column chromatography on silica gel
  2. washeluting with 20% methanol/chloroform
  3. customfollowed by recrystallization from hexanes/methylene chloride

Sources & evidence

ORD record
ord-19b9334f91ab49038c4cebe58e7fd6f7
Source dataset
uspto-grants-2002_05
Patent number
US06391878B2

Reaction notes

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