Trifluoroacetic acid → HCID 54303615, compound

HRID 849873Notes

Reaction equation

HRID 849873 reaction equation
C(OC(=O)[NH:7][C@@H:8]([C:20]1[N:24]([CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:23]=[N:22][N:21]=1)[CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:18]=[CH:19][C:10]=1[CH2:9][C@@H:8]([NH2:7])[C:20]1[N:24]([CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:23]=[N:22][N:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54448135HCID 54448135, compound

Product 1

HCID 54303615HCID 54303615, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

((1R)-2-(2-Naphthyl)-1-(1-phenethyl-1H-tetrazol-5-yl)ethyl)carbamic acid tert-butylester (0.30 g; 0.68 mmol) was dissolved in methylene chloride (20 ml) and trifluoroacetic acid (2 ml) was added. The mixture was stirred for 3 h at RT. The solvent was removed in vacuo and the residue was dissolved in methylene chloride (50 ml) and washed with sodium hydrogencarbonate (10%; 30 ml). The organic phase was dried (Magnesium sulfate) and the solvent removed in vacuo. The residue was chromatographed on silica (2.5×15 cm) using ethyl acetate as eluent to afford 170 mg of (1R)-2-(2-naphthyl)-1-(1-phenethyl-1H-tetrazol-5-yl)ethylamine.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in methylene chloride (50 ml)
  3. washwashed with sodium hydrogencarbonate (10%; 30 ml)
  4. dry with materialThe organic phase was dried (Magnesium sulfate)
  5. customthe solvent removed in vacuo
  6. customThe residue was chromatographed on silica (2.5×15 cm)

Sources & evidence

ORD record
ord-bfa4a87373c54036804fae2c1b5a0b37
Source dataset
uspto-grants-2000_01
Patent number
US06013658

Reaction notes

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