Trifluoroacetic acid → N-Sulfamoyl-N-(2-benzyloxy-4-bromo-6-fluorophenyl)glycine methyl ester

HRID 889244Notes

Reaction equation

HRID 889244 reaction equation
[CH3:1][O:2][C:3](=[O:33])[CH2:4][N:5]([S:22](=[O:32])(=[O:31])[NH:23]C(OC(C)(C)C)=O)[C:6]1[C:11]([F:12])=[CH:10][C:9]([Br:13])=[CH:8][C:7]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:33])[CH2:4][N:5]([S:22](=[O:31])(=[O:32])[NH2:23])[C:6]1[C:11]([F:12])=[CH:10][C:9]([Br:13])=[CH:8][C:7]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68429383HCID 68429383, compound

Product 1

HCID 68430976N-Sulfamoyl-N-(2-benzyloxy-4-bromo-6-fluorophenyl)glycine methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.25 g (2.28 mmol) of N-(t-butoxycarbonylsulfamoyl)-N-(2-benzyloxy-4-bromo-6-fluorophenyl)glycine methyl ester in 6 mL of methylene chloride is added 6 mL of TFA. The solution is stirred at room temperature for 20 min. then the solvent is removed under reduced pressure. The residual oil is purified by flash chromatography using 15% ethyl acetate in methylene chloride to elute the product as an oil: 1H NMR (CDCl3) δ 7.48-7.36 (m, 5H), 7.02-6.98 (m, 2H), 5.10 (d, J=4.30 Hz, 2H), 4.94 (s, 2H), 4.34 (q, 2H), 3.70 (s, 3H); MS (M−H)−=447.

Workup

  1. customthe solvent is removed under reduced pressure
  2. customThe residual oil is purified by flash chromatography
  3. washto elute the product as an oil

Sources & evidence

ORD record
ord-67ede0e34b61403bbeb3a1753f954d20
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Reaction notes

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