Hydrochloric Acid → 2-[(2,2,2-Trifluoroacetyl)amino]hexanoic acid

HRID 60413

Reaction equation

HRID 60413 reaction equation
[F:1][C:2]([F:8])([F:7])[C:3](OC)=[O:4].C([N:11](CC)CC)C.[CH2:16]([CH2:22][CH2:23]N)[CH2:17][CH2:18][C:19]([OH:21])=[O:20].Cl>CO.C(OCC)(=O)C>[F:8][C:2]([F:1])([F:7])[C:3]([NH:11][CH:18]([CH2:17][CH2:16][CH2:22][CH3:23])[C:19]([OH:21])=[O:20])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5646-Aminohexanoic AcidHCID 8471TriethylamineHCID 9893Methyl trifluoroacetate

Product 1

HCID 3035902-[(2,2,2-Trifluoroacetyl)amino]hexanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl trifluoroacetate (513 μL, 5.10 mmoles) and triethylamine (474 μL, 3.40 mmoles) were added to a suspension of aminocaproic acid (455 mg, 3.40 mmoles) in methanol (2 mL). After the mixture was stirred vigorously for 8 h, 1 N HCl was added dropwise until the a pH of 2 was obtained. The reaction was added to ethyl acetate (10 mL) was washed with 1 N HCl (2×2 mL), dried over MgSO4, and concentrated in vacuo to yield the amide as a white solid (745 mg, 3.49 mmoles, quant.). LRMS: not performed. 1H NMR: spectrum is consistent with the predicted structure.

Workup

  1. customwas obtained
  2. washwas washed with 1 N HCl (2×2 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e1173abdff0842da971a87694f4ce544
Source dataset
uspto-grants-2016_09
Patent number
US09440988B2

Linked notes

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