Potassium Carbonate → Methyl (2S)-2-(2,3,4-trifluoroanilino)propionate

HRID 985647Notes

Reaction equation

HRID 985647 reaction equation
[F:1][C:2]1[C:8]([F:9])=[C:7]([F:10])[CH:6]=[CH:5][C:3]=1[NH2:4].C(=O)([O-])[O-].[K+].[K+].CS(O[C@H:22]([CH3:27])[C:23]([O:25][CH3:26])=[O:24])(=O)=O>[Cl-].C([N+](CCCCCC)(CCCCCC)CCCCCC)CCCCC>[F:1][C:2]1[C:8]([F:9])=[C:7]([F:10])[CH:6]=[CH:5][C:3]=1[NH:4][C@@H:22]([CH3:27])[C:23]([O:25][CH3:26])=[O:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 774682,3,4-TrifluoroanilineHCID 57320743Methyl (2R)-2-[(methylsulfonyl)oxy]propanoate

Product 1

HCID 10125210Methyl (2S)-2-(2,3,4-trifluoroanilino)propionate

Reagents, catalysts & solvents 1

HCID 80021Tetrahexylammonium chlorideCatalyst

Procedure

In accordance with the process of Example 2, a condensation reaction was performed by using 2,3,4-trifluoroaniline (100 mg), potassium carbonate (188 mg), methyl (2R)-2-[(methanesulfonyl)oxy]propionate (78 mg) and tetrahexylammonium chloride (40 mg) to give the title compound as an oily substance. As the result of the analysis by reversed phase HPLC with the use of the compound of Example 1 as a specimen, the product corresponded to 38 mg (24%) of the title compound.

Workup

  1. customIn accordance with the process of Example 2, a condensation reaction

Sources & evidence

ORD record
ord-73f337dc2fd446a68f473a755a830729
Source dataset
uspto-grants-2005_03
Patent number
US06872823B1

Reaction notes

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