Trifluoroacetic acid → HCID 28336308, compound

HRID 1014229Notes

Reaction equation

HRID 1014229 reaction equation
[CH3:1][N:2]([CH3:23])[CH2:3][C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([O:21][CH3:22])=[C:11]([NH:13]C(=O)OC(C)(C)C)[CH:12]=1)=[O:5].FC(F)(F)C(O)=O>ClCCl>[NH2:13][C:11]1[CH:12]=[C:7]([NH:6][C:4](=[O:5])[CH2:3][N:2]([CH3:23])[CH3:1])[CH:8]=[CH:9][C:10]=1[O:21][CH3:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59441757HCID 59441757, compound

Product 1

HCID 28336308HCID 28336308, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1,1-dimethylethyl [5-[(N,N-dimethylglycyl)amino]-2-(methyloxy)phenyl]carbamate (0.44 g, 1.36 mmol) and trifluoroacetic acid (1.55 g, 13.6 mmol, Aldrich) in dichloromethane (50 mL) was stirred overnight at room temperature. The crude reaction was diluted with dichloromethane (100 mL), washed with saturated NaHCO3 (100 mL), evaporated under reduced pressure, and dried under high vacuum to provide N1-[3-amino-4-(methyloxy)phenyl]-N2,N2-dimethylglycinamide (0.29 g, 95%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.22 (s, 6H) 2.99 (s, 2 H) 3.80 (s, 3 H) 5.29 (s, 2 H) 6.68-6.74 (m, 1 H) 7.03 (d, J=8.61 Hz, 1H) 7.22 (d, J=2.38 Hz, 1 H) 9.49 (s, 1 H). ESIMS (M+H)+=224.

Workup

  1. customThe crude reaction
  2. washwashed with saturated NaHCO3 (100 mL)
  3. customevaporated under reduced pressure
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-5aabbb68ad2d4436ac14e35e28be9a17
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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