Trifluoroacetic acid → Ethyl 5-(aminomethyl)-3-isoxazolecarboxylate

HRID 2111675Notes

Reaction equation

HRID 2111675 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:10][C:11]([C:13]1[CH:17]=[C:16]([CH2:18][NH:19]C(OC(C)(C)C)=O)[O:15][N:14]=1)=[O:12])[CH3:9]>C(Cl)Cl>[CH2:8]([O:10][C:11]([C:13]1[CH:17]=[C:16]([CH2:18][NH2:19])[O:15][N:14]=1)=[O:12])[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10588096Ethyl 5-(N-Boc)aminomethylisoxazole-3-carboxylate

Product 1

HCID 10850588Ethyl 5-(aminomethyl)-3-isoxazolecarboxylateYield 154,615.797%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2.1 ml, 29 mmol) was added to a solution of 3-ethoxycarbonyl-5-[N-(tert-butyloxycarbonyl)aminomethyl]isoxazole (Method 73; 790 mg, 2.9 mmol) in DCM (15 ml). The mixture was stirred at ambient temperature for 4 hours then the volatiles removed by evaporation. The residue was triturated with diethyl ether to give the title compound (763 g, 93%). NMR (DMSO): 1.31 (t, 3H), 4.37 (m, 2H), 6.97 (s, 1H), 8.64 (s, 3H); m/z 171 (MH)+.

Workup

  1. customthe volatiles removed by evaporation
  2. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-34ef3640796c44f1805ea356ec1fdad8
Source dataset
uspto-grants-2009_04
Patent number
US07521453B2

Reaction notes

Loading…