Trifluoroacetic acid → (S)-2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylmethylammonium trifluoroacetate

HRID 412413Notes

Reaction equation

HRID 412413 reaction equation
C(OC(=O)[NH:10][CH2:11][C@H:12]1[C:16](=[O:17])[O:15][C:14]([CH3:19])([CH3:18])[O:13]1)C1C=CC=CC=1.C1CCC=CC=1.[C:27]([OH:33])([C:29]([F:32])([F:31])[F:30])=[O:28]>C(O)C.[Pd]>[F:30][C:29]([F:32])([F:31])[C:27]([O-:33])=[O:28].[CH3:18][C:14]1([CH3:19])[O:13][C@@H:12]([CH2:11][NH3+:10])[C:16](=[O:17])[O:15]1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 116051,3-CyclohexadieneHCID 67483545(S)-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylmethyl)carbamic acid benzyl ester

Product 1

HCID 86586053(S)-2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylmethylammonium trifluoroacetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The crude (S)-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylmethyl)carbamic acid benzyl ester (976 mg, 3.5 mmol) was dissolved in ethanol (14 mL), and palladium (10% on activated charcoal, 300 mg) and 1,3-cyclohexadiene (2.8 g, 35 mmol) were added and the reaction was stirred for 1 hour at room temperature, and heated to 40° C. for 10 min. After filtration, TFA (0.4 g, 3.5 mmol) was added and the solvent was removed by evaporation to afford crude (S)-2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylmethylammonium trifluoroacetate as an oil.

Workup

  1. temperatureheated to 40° C. for 10 min
  2. additionwas added
  3. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-14f4d440d99b445fa94bb3461e4c6255
Source dataset
uspto-grants-2003_05
Patent number
US06562807B2

Reaction notes

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