Trifluoroacetic acid → Ethyl 4-[15-(trifluoromethyl)pentadecylamino]benzoylacetate

HRID 1395729Notes

Reaction equation

HRID 1395729 reaction equation
[F:1][C:2]([F:41])([F:40])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]1[CH:39]=[CH:38][C:22]([C:23]([CH:25](C(OCC)=O)[C:26]([O:28][C:29](C)(C)[CH3:30])=[O:27])=[O:24])=[CH:21][CH:20]=1.FC(F)(F)C(O)=O.[OH-].[K+]>>[F:1][C:2]([F:40])([F:41])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]1[CH:39]=[CH:38][C:22]([C:23]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:24])=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14797Potassium HydroxideHCID 20549324tert-Butyl ethyl 4-[15-(trifluoromethyl)pentadecylamino]benzoylmalonate

Product 1

HCID 20549307Ethyl 4-[15-(trifluoromethyl)pentadecylamino]benzoylacetate

Procedure

A solution of 3.0 g. of tert-butyl ethyl 4-[15-(trifluoromethyl)pentadecylamino]benzoylmalonate and 10 ml. of trifluoroacetic acid is warmed with stirring for 3 hours. The solution is poured onto ice and neutralized with potassium hydroxide. The resulting precipitate is collected by filtration, washed with water and dried. Recrystallization from chloroform affords the product as a white solid.

Workup

  1. filtrationThe resulting precipitate is collected by filtration
  2. washwashed with water
  3. customdried
  4. customRecrystallization from chloroform

Sources & evidence

ORD record
ord-6c69ac2d71a24bee8327f15dac29ff49
Source dataset
uspto-grants-1980_05
Patent number
US04205085

Reaction notes

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