Trifluoroacetic acid methylene chloride → N-sulfamoyl-N-(2-benzyloxy-6-fluorophenyl)glycine methyl ester

HRID 889273Notes

Reaction equation

HRID 889273 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH2:4][N:5]([S:21](=[O:31])(=[O:30])[NH:22]C(OC(C)(C)C)=O)[C:6]1[C:11]([F:12])=[CH:10][CH:9]=[CH:8][C:7]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.FC(F)(F)C(O)=O.ClCCl>>[CH3:1][O:2][C:3](=[O:32])[CH2:4][N:5]([S:21](=[O:30])(=[O:31])[NH2:22])[C:6]1[C:11]([F:12])=[CH:10][CH:9]=[CH:8][C:7]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 68429517N-(t-butoxycarbonylsulfamoyl)-N-(2-benzyloxy-6-fluorophenyl)glycine methyl ester

Product 1

HCID 68430886N-sulfamoyl-N-(2-benzyloxy-6-fluorophenyl)glycine methyl ester

Procedure

A solution of N-(t-butoxycarbonylsulfamoyl)-N-(2-benzyloxy-6-fluorophenyl)glycine methyl ester (980 mg, 2.09 mmol) 10 mL of trifluoroacetic acid:dichloromethane(1:1) is stirred at RT for 15 min. The solvent is removed under reduced pressure and the residue chromatographed on an Isco Companion (80 g silica gel cartridge, 30-60% gradient of hexane/ethyl acetate) to give N-sulfamoyl-N-(2-benzyloxy-6-fluorophenyl)glycine methyl ester. MS (M−1)−: 367 NMR (CDCl3): δ 7.41 (m, 5H), 7.25 (m, 1H), 2.21 (m, 2H), 5.13 (d, 2H, J=5.0 Hz), 5.02 (br s, 2H), 4.39 (dd, J=32 and 19 Hz, 2H), 3.70 (s, 3H).

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe residue chromatographed on an Isco Companion (80 g silica gel cartridge, 30-60% gradient of hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d73e859afcb14abfb1b142aabee936fd
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Reaction notes

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