Trifluoroacetic acid → HCID 59909794, compound

HRID 2183078Notes

Reaction equation

HRID 2183078 reaction equation
[CH:1]1([CH2:5][CH2:6][CH2:7][C@@H:8]([C:17]2[O:18][CH:19]=[C:20]([C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[N:21]=2)[CH2:9][C:10]([O:12]C(C)(C)C)=[O:11])[CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([CH2:5][CH2:6][CH2:7][C@@H:8]([C:17]2[O:18][CH:19]=[C:20]([C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[N:21]=2)[CH2:9][C:10]([OH:12])=[O:11])[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59909743HCID 59909743, compound

Product 1

HCID 59909794HCID 59909794, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (3R)-6-cyclobutyl-3-{4-[(dimethylamino)carbonyl]-1,3-oxazol-2-yl}hexanoate (Preparation 120) (240 mg, 0.66 mmol) in dichloromethane (4 ml) was treated with trifluoroacetic acid (1.2 ml) and stirred at room temperature for 4 hours. The solvent was removed under reduced pressure and the residue azeotroped from toluene and dichloromethane. The oil was purified by column chromatography on silica gel eluting with 97:3:0.3 (dichloromethane:methanol:acetic acid) to afford the title compound as a white solid (161 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue azeotroped from toluene and dichloromethane
  3. customThe oil was purified by column chromatography on silica gel eluting with 97:3:0.3 (dichloromethane:methanol:acetic acid)

Sources & evidence

ORD record
ord-0be9a1a4a96d45dc9089889235ce1774
Source dataset
uspto-grants-2005_05
Patent number
US06897306B2

Reaction notes

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