Trifluoroacetic acid → HCID 67164197, compound

HRID 68627Notes

Reaction equation

HRID 68627 reaction equation
[C:1]1([CH2:7][O:8][C:9](=[O:61])[N:10]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([N:32]([CH2:47][C:48]3[N:49]([CH2:53][O:54][CH2:55][CH2:56][Si:57]([CH3:60])([CH3:59])[CH3:58])[CH:50]=[CH:51][N:52]=3)[CH2:33][C:34]3[N:35]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[CH:36]=[CH:37][N:38]=3)=[O:31])=[CH:26][CH:25]=2)[CH2:11][CH2:12][CH2:13][CH2:14][NH:15]C(OC(C)(C)C)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:15][CH2:14][CH2:13][CH2:12][CH2:11][N:10]([CH2:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]([N:32]([CH2:47][C:48]2[N:49]([CH2:53][O:54][CH2:55][CH2:56][Si:57]([CH3:59])([CH3:58])[CH3:60])[CH:50]=[CH:51][N:52]=2)[CH2:33][C:34]2[N:35]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:45])([CH3:44])[CH3:46])[CH:36]=[CH:37][N:38]=2)=[O:31])=[CH:28][CH:29]=1)[C:9](=[O:61])[O:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58300427Phenylmethyl({4-[(bis{[1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazol-2-yl]methyl}amino)carbonyl]phenyl}methyl)[4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)butyl]carbamate

Product 1

HCID 67164197HCID 67164197, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the compound 6 (225 mg), a solution of 25% trifluoroacetic acid in dichloromethane (6 mL) was added. The reaction mixture was stirred at room temperature for one hour. The reaction mixture was concentrated and the residue was added by 1N sodium hydroxide and then extracted with dichloromethane. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated. The obtained residue was purified by silica gel column chromatography (dichloromethane:methanol:28% ammonia water=80:10:1) to obtain the title compound (92 mg) having the following physical properties.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was added by 1N sodium hydroxide
  3. extractionextracted with dichloromethane
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe obtained residue was purified by silica gel column chromatography (dichloromethane:methanol:28% ammonia water=80:10:1)

Sources & evidence

ORD record
ord-f5144ad12b85486e916a7c5047510905
Source dataset
uspto-grants-2014_09
Patent number
US08822459B2

Reaction notes

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