Trifluoroacetic acid → 3-Cyclohexylmethyl-4-(4-isopropyl-2-oxooxazolidin-3-yl)-4-oxobutyric acid

HRID 1060744Notes

Reaction equation

HRID 1060744 reaction equation
[CH:1]1([CH2:7][CH:8]([C:17]([N:19]2[CH:23]([CH:24]([CH3:26])[CH3:25])[CH2:22][O:21][C:20]2=[O:27])=[O:18])[CH2:9][C:10]([O:12]C(C)(C)C)=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:1]1([CH2:7][CH:8]([C:17]([N:19]2[CH:23]([CH:24]([CH3:25])[CH3:26])[CH2:22][O:21][C:20]2=[O:27])=[O:18])[CH2:9][C:10]([OH:12])=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18628724Tert-butyl 3-cyclohexylmethyl-4-(4-isopropyl-2-oxooxazolidin-3-yl)-4-oxobutyrate

Product 1

HCID 186287363-Cyclohexylmethyl-4-(4-isopropyl-2-oxooxazolidin-3-yl)-4-oxobutyric acidYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 3-cyclohexylmethyl-4-(4-isopropyl-2-oxooxazolidin-3-yl)-4-oxobutyrate (2.90 g, 7.6 mmol) in methylene chloride (10 mL) was treated with trifluoroacetic acid (4.83 g, 42.5 mmol) and the mixture was stirred at ambient temperature for 3 hours. The solvent and excess acid were removed by evaporation at reduced pressure. The residue was dissolved in ether/hexane and product was crystallized out to provide 3-cyclohexylmethyl-4-(4-isopropyl-2-oxooxazolidin-3-yl)-4-oxobutyric acid (2 g, 81%). MS (M+1): 326.

Workup

  1. customThe solvent and excess acid were removed by evaporation at reduced pressure
  2. dissolutionThe residue was dissolved in ether/hexane
  3. customproduct was crystallized out

Sources & evidence

ORD record
ord-f2ae885608704711a9b9e677ff9d0aa0
Source dataset
uspto-grants-2003_02
Patent number
US06525036B2

Reaction notes

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