Ethanol → Trifluoroacetic acid

HRID 1993129Notes

Reaction equation

HRID 1993129 reaction equation
C([NH2:5])(C)(C)C.C(O)C.[C:9]([OH:15])([C:11]([F:14])([F:13])[F:12])=[O:10].[OH2:16]>>[OH:16][NH-:5].[C:9]([OH:15])([C:11]([F:14])([F:13])[F:12])=[O:10]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 6385Tert-ButylamineHCID 6422Trifluoroacetic acid

Product 2

HCID 6422Trifluoroacetic acidYield 51%HCID 178514248HCID 178514248, compound

Conditions

Temperature
60 °C

Procedure

A mixture of compound 25.4 (0.027 g), ethanol (1.5 mL), TFA (0.6 mL) and water (0.5 mL) was stirred at 60° C. for 18 h. The mixture was concentrated under reduced pressure, and the residue was purified by HPLC to afford compound 25.6 as a TFA salt (0.014 g, 51%). 1H NMR (CD3OD): δ 1.4 (t, J=8 Hz, 6H), 2.9 (M, 4H), 3.2 (m, 2H), 3.58 (brs, 2H), 3.65 (m, 2H), 4.25 (m, 4H), 4.42 (d, J=10 Hz, 2H), 4.85 (m, 2H), 6.75 (d, J=9 Hz, 2H), 6.9 (m, 4H), 7.0 (d, J=9 Hz, 2H), 7.4-7.6 (m, 6H), 8.1 (brs, 2H). 31P NMR (CD3OD): δ 20.8. MS: 769 (M+1).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-3fecfec6cfe84ce18960cfc206655fe0
Source dataset
uspto-grants-2010_01
Patent number
US07649015B2

Reaction notes

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