Trifluoroacetic acid → (3R)-6-Cyclohexyl-3-[4-(ethoxycarbonyl)-1,3-oxazol-2-yl]hexanoic acid trifluoroacetate

HRID 2183025Notes

Reaction equation

HRID 2183025 reaction equation
C([O:5][C:6](=[O:28])[CH2:7][C@H:8]([C:18]1[O:19][CH:20]=[C:21]([C:23]([O:25][CH2:26][CH3:27])=[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.[F:29][C:30]([F:35])([F:34])[C:31]([OH:33])=[O:32]>ClCCl>[F:29][C:30]([F:35])([F:34])[C:31]([OH:33])=[O:32].[CH:12]1([CH2:11][CH2:10][CH2:9][C@@H:8]([C:18]2[O:19][CH:20]=[C:21]([C:23]([O:25][CH2:26][CH3:27])=[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 59110691ethyl 2-[(1R)-1-(2-tert-butoxy-2-oxoethyl)-4-cyclohexylbutyl]-1,3-oxazole-4-carboxylate

Product 1

HCID 69778281(3R)-6-Cyclohexyl-3-[4-(ethoxycarbonyl)-1,3-oxazol-2-yl]hexanoic acid trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 2-{(1R)-1-[2-(tert-butoxy)-2-oxoethyl]-4-cyclohexylbutyl}-1,3-oxazole-4-carboxylate (Preparation 62) (1.58 g, 4.01 mmol) in anhydrous dichloromethane (25 ml) was treated with trifluoroacetic acid (7 ml) and the resulting mixture was stirred at room temperature under a nitrogen atmosphere for 4 hours. The solvent was removed under reduced pressure and the residue azeotroped from dichloromethane to afford the title compound (1.66 g).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue azeotroped from dichloromethane

Sources & evidence

ORD record
ord-808674dc37154f7aad61d7b0a649b6ff
Source dataset
uspto-grants-2005_05
Patent number
US06897306B2

Reaction notes

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