Triethylamine → 1-(2,2,2-Trifluoroacetamido)cyclopropane-1-carboxylic acid

HRID 2055573Notes

Reaction equation

HRID 2055573 reaction equation
[Cl-].[C:2]([C:5]1([NH3+:8])[CH2:7][CH2:6]1)([OH:4])=[O:3].C(N(CC)CC)C.[F:16][C:17]([F:24])([F:23])[C:18](OCC)=[O:19]>CO>[F:16][C:17]([F:24])([F:23])[C:18]([NH:8][C:5]1([C:2]([OH:4])=[O:3])[CH2:7][CH2:6]1)=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9794Ethyl trifluoroacetateHCID 1101893268781-13-5

Product 1

HCID 129888001-(2,2,2-Trifluoroacetamido)cyclopropane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

1-Carboxycyclopropanaminium chloride (0.980 g, 7.124 mmol) was suspended in methanol (14 mL) and triethylamine (1.514 g, 14.960 mmol) was subsequently added. To this suspension was then added ethyl trifluoroacetate (1.113 g, 7.836 mmol) and allowed to stir at 25° C. After 16 hours, the reaction was quenched with 1N hydrochloric acid and extracted with ethyl acetate. The organic extract was dried with sodium sulfate, filtered and concentrated under reduced pressure to produce the title compound as a white solid. 1H NMR (400 MHz, (CD3)2SO) δ 12.76 (s, 1H), 9.94 (s, 1H), 1.38-1.44 (m, 2H), 1.08-1.14 (m, 2H).

Workup

  1. customthe reaction was quenched with 1N hydrochloric acid
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1c01a7c6217546f29e3b605de2f91097
Source dataset
uspto-grants-2008_02
Patent number
US07332499B2

Reaction notes

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