Trifluoroacetic acid → HCID 178520538, compound

HRID 368784Notes

Reaction equation

HRID 368784 reaction equation
[CH2:1]([CH:8]([C:20]1[N:24](CC2C=CC(OC)=CC=2)[N:23]=[N:22][N:21]=1)[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>O>[CH2:1]([CH:8]([C:20]1[NH:24][N:23]=[N:22][N:21]=1)[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23288311HCID 23288311, compound

Product 1

HCID 178520538HCID 178520538, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-[1-benzyl-3-(3,4-dichlorophenyl)-3-oxo-propyl]-1(4-methoxybenzyl)-1H-tetrazole (1.6 g, 3.3 mmol), from the previous step) and TFA (20 ml) were mixed and stirred at room temperature under nitrogen atmosphere for 40 hours. The mixture was diluted with water (100 ml) and extracted with methylene chloride (3×200 ml). The organic layers were combined, washed with water (2×100 ml), brine (1×100 ml) and dried over anhydrous sodium sulphate. The solvent was removed under vacuum and the residue was flash chromatographed by using cyclohexane/ethyl acetate 0÷20 as eluent. The title compound was obtained as a colourless solid (0.6 g, 50%) (m.p. 172°-174° C.).

Workup

  1. extractionextracted with methylene chloride (3×200 ml)
  2. washwashed with water (2×100 ml), brine (1×100 ml)
  3. dry with materialdried over anhydrous sodium sulphate
  4. customThe solvent was removed under vacuum
  5. customchromatographed

Sources & evidence

ORD record
ord-e1374b290ee248c2ae2d258b11034ca2
Source dataset
uspto-grants-2000_10
Patent number
US06133302

Reaction notes

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