Trifluoroacetic acid → HCID 23301490, compound

HRID 1952972Notes

Reaction equation

HRID 1952972 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]([C:22]1[N:26]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[C:25]2[CH:35]=[CH:36][CH:37]=[CH:38][C:24]=2[N:23]=1)[CH2:10][CH2:11][CH2:12][N:13]([CH3:21])[C:14]([O:16]C(C)(C)C)=O.C(=O)([O-])[O-].[K+].[K+].[F:45][C:46]([F:69])([F:68])[C:47]1[CH:48]=[C:49]([CH:61]=[C:62]([C:64]([F:67])([F:66])[F:65])[CH:63]=1)[CH2:50][NH:51]C(=O)OC1C=CC=CC=1.[ClH:70].C(O)C>C(O)C.C(Cl)(Cl)Cl.O>[ClH:70].[CH3:8][N:9]([C:22]1[N:26]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[C:25]2[CH:35]=[CH:36][CH:37]=[CH:38][C:24]=2[N:23]=1)[CH2:10][CH2:11][CH2:12][N:13]([CH3:21])[C:14]([NH:51][CH2:50][C:49]1[CH:61]=[C:62]([C:64]([F:65])([F:66])[F:67])[CH:63]=[C:47]([C:46]([F:45])([F:68])[F:69])[CH:48]=1)=[O:16]

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 15480090HCID 15480090, compoundHCID 21887872Ethanol hydrochlorideHCID 23301493HCID 23301493, compound

Product 1

HCID 23301490HCID 23301490, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

2 ml of trifluoroacetic acid was added to 1.3 g of N-methyl-N-(1-(4-fluorobenzyl)benzimidazol-2-yl)-N'-methyl-N'-t-butoxycarbonyl-1,3-propylenediamine, and the mixture was stirred at room temperature for one hour. Then, 50 ml of water and 50 ml of chloroform were added thereto, and potassium carbonate was added thereto until the mixture became basic. The organic layer was taken and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, to obtain 970 mg of a colorless oily substance. To 300 mg of this oily substance, 370 mg of phenyl N-(3,5-bis(trifluoromethyl)benzyl)carbamate was added, and the mixture was heated and stirred at 120° C. for two hours. After cooling, the obtained oily substance was purified by silica gel column chromatography (eluent: ethyl acetate/ethanol=9/1) to obtain 500 mg of a colorless oily substance. 250 mg of this oily substance was dissolved in 3 ml of ethanol, and 1 ml of 28% hydrochloric acid-ethanol was added thereto. The solvent was distilled off under reduced pressure, and the residue was crystallized from diethyl ether to obtain 280 mg of the above identified compound as colorless crystals. (m.p. 170.0-172.0° C.)

Workup

  1. dry with materialdried over anhydrous sodium sulfate
  2. distillationThe solvent was distilled off under reduced pressure
  3. customto obtain 970 mg of a colorless oily substance
  4. temperaturethe mixture was heated
  5. stirringstirred at 120° C. for two hours
  6. temperatureAfter cooling
  7. customthe obtained oily substance was purified by silica gel column chromatography (eluent: ethyl acetate/ethanol=9/1)
  8. customto obtain 500 mg of a colorless oily substance
  9. distillationThe solvent was distilled off under reduced pressure
  10. customthe residue was crystallized from diethyl ether
  11. customto obtain 280 mg of the

Sources & evidence

ORD record
ord-c7844d3bc5dd4c6283f918bd61d79495
Source dataset
uspto-grants-2000_09
Patent number
US06114369

Reaction notes

Loading…