Hydrochloric Acid → N-[4-Cyano-3-(trifluoromethyl)phenyl]-N-(2,2,2-trifluoroethyl)-L-alanine

HRID 2109084Notes

Reaction equation

HRID 2109084 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:16][C:17]([F:20])([F:19])[F:18])[C@H:10]([C:12]([O:14]C)=[O:13])[CH3:11])=[CH:5][C:4]=1[C:21]([F:24])([F:23])[F:22])#[N:2].[OH-].[Na+].Cl>C1COCC1.CO>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:16][C:17]([F:18])([F:19])[F:20])[C@H:10]([C:12]([OH:14])=[O:13])[CH3:11])=[CH:5][C:4]=1[C:21]([F:22])([F:24])[F:23])#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11772599HCID 11772599, compound

Product 1

HCID 71413886N-[4-Cyano-3-(trifluoromethyl)phenyl]-N-(2,2,2-trifluoroethyl)-L-alanineYield 100%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl N-[4-cyano-3-(trifluoromethyl)phenyl]-N-(2,2,2-trifluoroethyl)alaninate (0.034 g, 0.11 mmol) in THF:methanol (1:1; 3 mL) was added 1N NaOH (1.1 ml, 1.1 mmol). The solution was heated at 60° C. for 30 min. Upon cooling, the solution was treated with 1N HCl (5 mL) and partitioned between ethyl acetate and saturated brine. The organic phase was washed with brine, dried (Na2SO4), and concentrated in vacuo to give 0.031 g (100% yield) of the desired product as a white solid: 1H NMR (400 MHz, CDCl3) δ 7.69 (d, J=8.8 Hz, 1H), 7.13 (d, J=2.7 Hz, 1H), 6.98 (dd, J=8.8, 2.7 Hz, 1H), 4.55 (q, J=7.2 Hz, 1H), 4.17-4.01 (m, 2H), 1.69 (d, J=7.2 Hz, 3H).

Workup

  1. temperatureUpon cooling
  2. custompartitioned between ethyl acetate and saturated brine
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2b1b11bbe8c241039512e312765e4ef3
Source dataset
uspto-grants-2009_04
Patent number
US07514470B2

Reaction notes

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