Methanol → N-[4-(Trifluoromethyl)phenyl]glycine

HRID 1373076Notes

Reaction equation

HRID 1373076 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)C.CO.O1CCCC1.O.[OH-].[Li+]>O>[F:14][C:13]([F:15])([F:16])[C:10]1[CH:11]=[CH:12][C:7]([NH:6][CH2:5][C:4]([OH:17])=[O:3])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 302677(4-trifluoromethyl-phenylamino)-acetic acid ethyl ester

Product 1

HCID 22250321N-[4-(Trifluoromethyl)phenyl]glycineYield 100.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of (4-trifluoromethyl-phenylamino)-acetic acid ethyl ester (0.37 g, 1.5 mmol) in a mixed solvent of methanol (10 mL), tetrahydrofuran (10 mL), and water (10 mL) was added lithium hydroxide monohydrate (0.25 g, 6 mmol) and the mixture was stirred at room temperature overnight. The organic solvent was removed under reduced pressure and the aqueous solution was acidified with solid citric acid to pH˜4, and extracted with ethyl acetate (4×40 mL). The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated to give 0.33 g of the crude title compound that was used direct for the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ: 12.68 (s, 1H), 7.38 (d, 2H), 6.66 (d, 2H), 3.87 (s, 2H).

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. extractionextracted with ethyl acetate (4×40 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-174f4715e2fd4c4e85aa1627d149110c
Source dataset
uspto-grants-2007_01
Patent number
US07160902B2

Reaction notes

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