Hydrochloric Acid → N-(trifluoroacetyl)aminoacetic acid

HRID 11902

Reaction equation

HRID 11902 reaction equation
[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]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 8471TriethylamineHCID 9893Methyl trifluoroacetate

Product 1

HCID 136227N-(trifluoroacetyl)aminoacetic acidYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-2b7d1cffff564c4a9cb1d06f37c1aa66
Source dataset
uspto-grants-2006_08
Patent number
US07098196B1

Linked notes

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