Trifluoroacetic acid → HCID 9849492, compound

HRID 1450603Notes

Reaction equation

HRID 1450603 reaction equation
[CH2:1]([C:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[C:16]([C:21]([O:23]C(C)(C)C)=[O:22])=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:11][CH:10]=2)[C:6]2[CH:28]=[C:29]([C:33]3[N:37]([CH3:38])[C:36]4[CH:39]=[CH:40][C:41]([F:43])=[CH:42][C:35]=4[N:34]=3)[CH:30]=[C:31]([CH3:32])[C:5]=2[N:4]=1)[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([C:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[C:16]([C:21]([OH:23])=[O:22])=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:11][CH:10]=2)[C:6]2[CH:28]=[C:29]([C:33]3[N:37]([CH3:38])[C:36]4[CH:39]=[CH:40][C:41]([F:43])=[CH:42][C:35]=4[N:34]=3)[CH:30]=[C:31]([CH3:32])[C:5]=2[N:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67708481HCID 67708481, compound

Product 1

HCID 9849492HCID 9849492, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.4 g (2.4 mMol) of tert.butyl 4'-[(2-ethyl-4-methyl-6-(1-methyl-5-fluoro-benzimidazol-2-yl)-benzimidazol-1-yl)-methyl]-biphenyl-2-carboxylate and 15 ml of trifluoroacetic acid in 30 ml of methylene chloride is stirred for 14 hours at ambient temperature, then concentrated by evaporation, the residue is mixed with about 30 ml of water and made alkaline with 2N sodium hydroxide solution. After extracting twice with 30 ml of diethyl ether, the aqueous phase is acidified with 20% citric acid. The crude product precipitated is suction filtered and purified by column chromatography (100 g silica gel; eluant:methylene chloride/ethanol=96:4).

Workup

  1. concentrationconcentrated by evaporation
  2. additionthe residue is mixed with about 30 ml of water
  3. extractionAfter extracting twice with 30 ml of diethyl ether
  4. customThe crude product precipitated
  5. filtrationfiltered
  6. custompurified by column chromatography (100 g silica gel; eluant:methylene chloride/ethanol=96:4)

Sources & evidence

ORD record
ord-2bd3b9e3e0204978b8b5841be0e235bf
Source dataset
uspto-grants-1997_02
Patent number
US05602127

Reaction notes

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