Trifluoroacetic acid → Ethyl 3-fluoro-4-(hexadecylamino)benzoylacetate

HRID 1389106Notes

Reaction equation

HRID 1389106 reaction equation
FC(F)(F)C(O)=O.[OH-].[K+].[F:10][C:11]1[CH:12]=[C:13]([CH:29]=[CH:30][C:31]=1[NH:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[C:14]([CH:16](C(OCC)=O)[C:17]([O:19][C:20](C)(C)[CH3:21])=[O:18])=[O:15]>>[F:10][C:11]1[CH:12]=[C:13]([CH:29]=[CH:30][C:31]=1[NH:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[C:14]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:15]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14797Potassium HydroxideHCID 53991576Tert-butyl ethyl 3-fluoro-4-(hexadecylamino)benzoylmalonate

Product 1

HCID 20536531Ethyl 3-fluoro-4-(hexadecylamino)benzoylacetate

Procedure

A solution of 3.0 g. of tert-butyl ethyl 3-fluoro-4-(hexadecylamino)benzoylmalonate 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 ethyl 3-fluoro-4-(hexadecylamino)benzoylacetate.

Workup

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

Sources & evidence

ORD record
ord-bd9f801642eb45c6b1eb2121e447b1aa
Source dataset
uspto-grants-1981_01
Patent number
US04243609

Reaction notes

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