Hydrochloric Acid → 6-(Trifluoroacetamido)hexanoic Acid

HRID 974164Notes

Reaction equation

HRID 974164 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17].C(N(CC)CC)C.Cl.[Cl-].[Na+]>CO.C(Cl)Cl>[F:9][C:2]([F:1])([F:8])[C:3]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[O:5]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5646-Aminohexanoic AcidHCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 9794Ethyl trifluoroacetate

Product 1

HCID 3035936-(Trifluoroacetamido)hexanoic AcidYield 57.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Ethyl trifluoroacetate (7.1 g, 50 mmole) is added with stirring to a suspension of 6-aminocaproic acid (I, 5.0 g, 40 mmole) in methanol (25 ml) and triethylamine (40 mmole) is added, with stirring. After stirring for 12 hours, by which time all the acid is in solution, the mixture is diluted with methylene chloride (100 ml) and made acidic (pH 1) with 1 N HCl. Saturated sodium chloride solution (90 ml) is then added and the lower layer is separated. The aqueous layer is extracted with methylene chloride (100 ml) and the two organic extracts are combined, dried over sodium sulfate and the solvents evaporated to afford 5.21 g of the desired acid II (Scheme I).

Workup

  1. additionis added
  2. stirringAfter stirring for 12 hours, by which time all the acid
  3. customthe lower layer is separated
  4. extractionThe aqueous layer is extracted with methylene chloride (100 ml)
  5. dry with materialdried over sodium sulfate
  6. customthe solvents evaporated

Sources & evidence

ORD record
ord-efa16be0eecd4e149b62958fe5654712
Source dataset
uspto-grants-1991_11
Patent number
US05068227

Reaction notes

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