N-(t-Butoxycarbonylsulfamoyl)-N-(2-benzyloxy-4-phenoxyphenyl)glycine methyl ester → N-Sulfamoyl-N-(2-benzyloxy-4-phenoxyphenyl)glycine methyl ester

HRID 1642627Notes

Reaction equation

HRID 1642627 reaction equation
[CH3:1][O:2][C:3](=[O:38])[CH2:4][N:5]([S:27](=[O:37])(=[O:36])[NH:28]C(OC(C)(C)C)=O)[C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][C:7]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:38])[CH2:4][N:5]([S:27](=[O:37])(=[O:36])[NH2:28])[C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:8][C:7]=1[O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

3

Reactant 1

HCID 66757056N-(t-Butoxycarbonylsulfamoyl)-N-(2-benzyloxy-4-phenoxyphenyl)glycine methyl ester

Product 1

HCID 66756634N-Sulfamoyl-N-(2-benzyloxy-4-phenoxyphenyl)glycine methyl ester

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of N-(t-butoxycarbonylsulfamoyl)-N-(2-benzyloxy-4-phenoxyphenyl)glycine methyl ester (0.375 g, 0.69 mmol) in 6 mL TFA/DCM (1:1) is stirred at ambient temperature for 20 min. The solvent is removed under reduced pressure. Methylene chloride is added to the residue and removed under reduced pressure. The resulting oil is purified by flash chromatography using 10% EtOAc/DCM to elute N-sulfamoyl-N-(2-benzyloxy-4-phenoxyphenyl)glycine methyl ester as an oil: 1H NMR (CDCl3) δ 7.44 (d, J=8.59 Hz, 1H), 7.33-7.26 (m, 7H), 7.09 (t, 1H), 6.97-6.93 (m, 2H), 6.60 (d, J=2.52 Hz, 1H), 6.43 (dd, J=8.59, 2.53 Hz, 1H), 4.96 (s, 2H), 4.26 (s, 2H), 3.62 (s, 3H); MS (M−H)−=441.

Workup

  1. customThe solvent is removed under reduced pressure
  2. additionMethylene chloride is added to the residue
  3. customremoved under reduced pressure
  4. customThe resulting oil is purified by flash chromatography
  5. washto elute N-sulfamoyl-N-(2-benzyloxy-4-phenoxyphenyl)glycine methyl ester as an oil

Sources & evidence

ORD record
ord-02ef82ce05824ac9b51363c558a5addd
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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