Trifluoroacetic acid → N-[4-Cyano-3-(trifluoromethyl)phenyl]-N-(cyclopropylmethyl)glycine

HRID 2109072Notes

Reaction equation

HRID 2109072 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:18][CH:19]2[CH2:21][CH2:20]2)[CH2:10][C:11]([O:13]C(C)(C)C)=[O:12])=[CH:5][C:4]=1[C:22]([F:25])([F:24])[F:23])#[N:2].C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:18][CH:19]2[CH2:20][CH2:21]2)[CH2:10][C:11]([OH:13])=[O:12])=[CH:5][C:4]=1[C:22]([F:23])([F:25])[F:24])#[N:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 113142081,1-Dimethylethyl N-[4-cyano-3-(trifluoromethyl)phenyl]-N-(cyclopropylmethyl)glycinate

Product 1

HCID 11369986N-[4-Cyano-3-(trifluoromethyl)phenyl]-N-(cyclopropylmethyl)glycineYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1,1-dimethylethyl N-[4-cyano-3-(trifluoromethyl)phenyl]-N-(cyclopropylmethyl)glycinate (5.01 g, 14.1 mmol), TFA (50 mL), and triethylsilane (5 mL) in CH2Cl2 (50 mL) was stirred at ambient temperature for 3 h. When the TLC indicated no remaining starting material, the solvents were removed under reduced pressure, and the residue was stirred in hexane (50 mL) for 12 hours. The solid precipitate was filtered and dried to obtain 2.9 g (71%) of the title compound as a white solid: 1H NMR (400 MHz, CDCl3) δ 7.61 (d, J=8.8 Hz, 1H), 6.97 (d, J=2.8 Hz, 1H), 6.78 (dd, J=8.8, 2.8 Hz, 1H), 4.29 (s, 2H), 3.34 (d, J=6.4 Hz, 2H), 1.37 (m, 1H), 0.64 (m, 2H), 0.27 (m, 2H).

Workup

  1. customthe solvents were removed under reduced pressure
  2. stirringthe residue was stirred in hexane (50 mL) for 12 hours
  3. filtrationThe solid precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-f3c12380df1d4f4580b5d24a61ac5daf
Source dataset
uspto-grants-2009_04
Patent number
US07514470B2

Reaction notes

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