Trifluoroacetic acid → HCID 69778303, compound

HRID 1279877Notes

Reaction equation

HRID 1279877 reaction equation
C([O:5][C:6](=[O:37])[CH2:7][C@H:8]([C:18]1[O:22][N:21]=[C:20]([CH2:23][CH:24](C(OCC)=O)[C:25]([O:27][C:28](C)(C)[CH3:29])=[O:26])[N:19]=1)[CH2:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH:12]1([CH2:11][CH2:10][CH2:9][C@@H:8]([C:18]2[O:22][N:21]=[C:20]([CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:19]=2)[CH2:7][C:6]([OH:37])=[O:5])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69778548HCID 69778548, compound

Product 1

HCID 69778303HCID 69778303, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-tert-butyl 3-ethyl 2-({5-[(1R)-1-(2-tert-butoxy-2-oxoethyl)-4-cyclohexylbutyl]-1,2,4-oxadiazol-3-yl}methyl)malonate (Preparation 93) (510 mg, 0.79 mmol) in dichloromethane (10 ml) was treated with trifluoroacetic acid (5 ml) and stirred at room temperature for 5 hours. The solvent was removed under reduced pressure and the residue azeotroped from toluene. The solid was dissolved in xylene (10 ml) and heated at 140° C. for 7 hours. The solvent was removed under reduced pressure. The oil was purified by column chromatography on silica gel eluting with a gradient system of 95:5:0 (dichloromethane:isopropyl alcohol:acetic acid) gradually changing to 90:10:1 (dichloromethane:isopropyl alcohol:acetic acid) to afford the title compound as a colourless oil (117 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue azeotroped from toluene
  3. dissolutionThe solid was dissolved in xylene (10 ml)
  4. temperatureheated at 140° C. for 7 hours
  5. customThe solvent was removed under reduced pressure
  6. customThe oil was purified by column chromatography on silica gel eluting with a gradient system of 95:5:0 (dichloromethane:isopropyl alcohol:acetic acid)

Sources & evidence

ORD record
ord-1d204179f5234e3da5b9fbffb456a6ff
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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