Hydrochloric Acid → N-(trifluoroacetyl)aminoacetic acid

HRID 1454118

Reaktionsgleichung

Reaktionsgleichung von HRID 1454118
[F:1][C:2]([F:8])([F:7])[C:3](OC)=[O:4].C(N(CC)CC)C.[NH2:16][CH2:17][C:18]([OH:20])=[O:19].Cl>CO.C(OCC)(=O)C>[F:8][C:2]([F:1])([F:7])[C:3]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:4]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 8471TriethylamineHCID 9893Methyl trifluoroacetate

Produkt 1

HCID 136227N-(trifluoroacetyl)aminoacetic acidAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Methyl trifluoroacetate (804 μL, 7.99 mmoles) and triethylamine (928 μL, 6.66 mmoles) were added to a suspension of glycine (500 mg, 6.66 mmoles) in methanol (2.5 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 (30 mL) was washed with 1 N HCl (2×10 mL), dried over MgSO4, and concentrated in vacuo to yield the amide as a white solid (991 mg, 5.79 mmoles, 87%). LRMS: (CI+) calcd for C4H4NO3F3(M+NH4): 189; found: 189. 1H NMR: spectrum is consistent with the predicted structure.

Aufarbeitung

  1. customwas obtained
  2. washwas washed with 1 N HCl (2×10 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1d0bcf48d42e403aba140d3e296f609b
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07476661B2

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