Trifluoroacetic acid → HCID 59909762, compound

HRID 1350281Notes

Reaction equation

HRID 1350281 reaction equation
C([O:5][C:6](=[O:28])[CH2:7][C@H:8]([C:18]1[O:19][C:20]([CH3:27])=[C:21]([C:23]([O:25][CH3:26])=[O:24])[N:22]=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:19][C:20]([CH3:27])=[C:21]([C:23]([O:25][CH3:26])=[O:24])[N:22]=2)[CH2:7][C:6]([OH:28])=[O:5])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59909851HCID 59909851, compound

Product 1

HCID 59909762HCID 59909762, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 2-{(1R)-1-[2-(tert-butoxy)-2-oxoethyl]-4-cyclohexylbutyl}-5-methyl-1,3-oxazole-4-carboxylate (Preparation 173) (2.92 g, 7.43 mmol) in anhydrous dichloromethane (15 ml) was treated with trifluoroacetic acid (7.5 ml) and the resulting mixture was stirred at room temperature under a nitrogen atmosphere for 24 hours. The solvent was removed under reduced pressure and the residue was azeotroped with dichloromethane (×3). The residue was purified by column chromatography on silica gel eluting with a gradient system of ethyl acetate:pentane (0:100 to 40:60) to afford the title compound as a colourless oil (2.50 g).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was azeotroped with dichloromethane (×3)
  3. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of ethyl acetate:pentane (0:100 to 40:60)

Sources & evidence

ORD record
ord-2396081cf31b466db58a9c878224be4a
Source dataset
uspto-grants-2007_05
Patent number
US07214694B2

Reaction notes

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