Methyl 2-(4-chlorophenyl)-3-(2,2,2-trifluoroethylamino)propanoate → Potassium 2-(4-chlorophenyl)-3-(2,2,2-trifluoroethylamino)propanoate

HRID 2200300Notes

Reaction equation

HRID 2200300 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:13][NH:14][CH2:15][C:16]([F:19])([F:18])[F:17])[C:9]([O:11]C)=[O:10])=[CH:4][CH:3]=1.O([Si](C)(C)C)[K:21]>C1COCC1.CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:13][NH:14][CH2:15][C:16]([F:17])([F:18])[F:19])[C:9]([O-:11])=[O:10])=[CH:6][CH:7]=1.[K+:21]

Participants

5

Reactant 2

HCID 66617993Methyl 2-(4-chlorophenyl)-3-(2,2,2-trifluoroethylamino)propanoateHCID 178504318HCID 178504318, compound

Product 1

HCID 66617976Potassium 2-(4-chlorophenyl)-3-(2,2,2-trifluoroethylamino)propanoateYield 118%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-(4-chlorophenyl)-3-(2,2,2-trifluoroethylamino)propanoate (235 mg, 0.795 mmol) in THF (3.0 mL) was treated with KOTMS (153 mg, 1.19 mmol) at room temperature. The reaction was allowed to stir 18 hours to completion, and the mixture was diluted with ether. The resulting precipitate was isolated by filtration and placed under high vacuum for two hours to afford the potassium 2-(4-chlorophenyl)-3-(2,2,2-trifluoroethylamino)propanoate (299 mg, 118%, excess salts) as a white solid. LCMS (APCI+) m/z 282.0 [M+H]+.

Workup

  1. customThe resulting precipitate was isolated by filtration
  2. waitplaced under high vacuum for two hours

Sources & evidence

ORD record
ord-63cf19e9b31945f2b93b80dce041414d
Source dataset
uspto-grants-2016_06
Patent number
US09359340B2

Reaction notes

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