6-Aminohexanoic Acid → 6-(Trifluoroacetamido)hexanoic Acid

HRID 1825704Notes

Reaction equation

HRID 1825704 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].C(N(CC)CC)C.[F:17][C:18]([F:25])([F:24])[C:19](OCC)=[O:20]>CO>[F:17][C:18]([F:25])([F:24])[C:19]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])=[O:20]

Participants

5

Reactant 3

HCID 5646-Aminohexanoic AcidHCID 8471TriethylamineHCID 9794Ethyl trifluoroacetate

Product 1

HCID 3035936-(Trifluoroacetamido)hexanoic AcidYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Aminocaproic acid (1, 6.55 g, 50 mmol) was suspended in methanol (30 ml) and treated with triethylamine (6.9 ml, 100 mmol) followed by ethyl trifluoroacetate (7.2 ml, 60 mmol). The mixture was stirred at room temperature (r.t.) during 40 hours. The unreacted solid precipitate was filtered, the filtrate was evaporated in vacuo and crystallized from benzene-hexane mixture. Trifluoroacetyl derivative (2) had an 84% yield (9.5 g).

Workup

  1. filtrationThe unreacted solid precipitate was filtered
  2. customthe filtrate was evaporated in vacuo
  3. customcrystallized from benzene-hexane mixture

Sources & evidence

ORD record
ord-fc39e95fb3e3414984008ccc023857ab
Source dataset
uspto-grants-2006_05
Patent number
US07049073B2

Reaction notes

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