tert-Butyl (2S)-2-{5-[1-(4-fluorophenyl)-2-(imidazol-1-yl)ethoxy]-2-(4-fluorophenethyl)benzoylamino}-4-methylsulfonylbutyrate → Ether isohexane

HRID 1251894Notes

Reaction equation

HRID 1251894 reaction equation
F[C:2]1C=[CH:6][C:5]([CH:8]([O:15][C:16]2C=CC(CCC3C=CC(F)=CC=3)=C([CH:38]=2)C(N[C@@H](CCS(C)(=O)=O)C(OC(C)(C)C)=O)=O)CN2C=CN=C2)=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O>[CH2:8]([O:15][CH2:16][CH3:38])[CH3:5].[CH3:2][CH2:3][CH2:4][CH:5]([CH3:8])[CH3:6]

Participants

3

Reactant 1

HCID 57318515tert-Butyl (2S)-2-{5-[1-(4-fluorophenyl)-2-(imidazol-1-yl)ethoxy]-2-(4-fluorophenethyl)benzoylamino}-4-methylsulfonylbutyrate

Product 1

HCID 21882825Ether isohexane

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl (2S)-2-{-5-[1-(4-fluorophenyl)-2-(imidazol-1-yl)ethoxy]-2-(4-fluorophenethyl)benzoylamino}-4-methylsulfonylbutyrate, (88 mg, 0.13 mmol) in TFA (2 ml), was stirred and cooled in an ice-bath for 3 hours. The TFA was removed by evaporation, the residue was dissolved in ethyl acetate and 1M HCl/diethylether (5 ml). Removal of the solvent gave a brown oil which on trituration with diethylether/iso-hexane (3×) gave the HCl salt of the title compound as a sticky white solid (40 mg).

Workup

  1. temperaturecooled in an ice-bath for 3 hours
  2. customThe TFA was removed by evaporation
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-b8633e6f86e442be9b4179728ec86f18
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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