Hydrochloric Acid → 12-(2,2,2-Trifluoroacetamido)dodecanoic acid

HRID 60411

Reaktionsgleichung

Reaktionsgleichung von HRID 60411
[F:1][C:2]([F:8])([F:7])[C:3](OC)=[O:4].C(N(CC)CC)C.[NH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29].Cl>CO.C(OCC)(=O)C>[F:8][C:2]([F:1])([F:7])[C:3]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[O:4]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 9893Methyl trifluoroacetateHCID 6966112-Aminododecanoic Acid

Produkt 1

HCID 2197255712-(2,2,2-Trifluoroacetamido)dodecanoic acidAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Methyl trifluoroacetate (200 μL, 1.99 mmoles) and triethylamine (184 μL, 1.32 mmoles) were added to a suspension of 12-aminododecanoic acid (300 mg, 1.32 mmoles) in methanol (2 mL). After the mixture was stirred vigorously for 18 h, 1 N HCl was added dropwise until the a pH of 2 was obtained. The reaction was added to ethyl acetate (20 mL) was washed with 1 N HCl (2×5 mL), dried over MgSO4, and concentrated in vacuo to yield the amide as a white solid (398 mg, 1.28 mmoles, 97%). LRMS: not performed. 1H NMR: spectrum is consistent with the predicted structure.

Aufarbeitung

  1. customwas obtained
  2. washwas washed with 1 N HCl (2×5 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e8d3cecc35b4472b9f4d76ad1a84f3e0
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440988B2

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