HCID 67138315, compound → HCID 67138567, compound

HRID 1592026Notes

Reaction equation

HRID 1592026 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][N:5]([S:16](=[O:26])(=[O:25])[NH:17]C(OC(C)(C)C)=O)[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[O:14][CH3:15]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:27])[CH2:4][N:5]([S:16](=[O:25])(=[O:26])[NH2:17])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[O:14][CH3:15]

Participants

3

Reactant 1

HCID 67138315HCID 67138315, compound

Product 1

HCID 67138567HCID 67138567, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of 1.7 g (4.2 mmol) of the title B compound, N-(t-butoxycarbonyl-sulfamoyl)-N-(2,4-dimethoxyphenyl)glycine methyl ester in 9 mL of TFA/CH2Cl2 (1:1) is stirred at RT for 30 min. The solvent is removed under reduced pressure. CH2Cl2 is added to the residue and the solvent is removed under reduced pressure. The resulting oil is purified by chromatography using 10% EtOAc in CH2Cl2 as the eluant to afford N-sulfamoyl-N-(2,4-dimethoxyphenyl)glycine methyl ester as an oil which crystallizes on standing: mp=100-103° C.; 1H-NMR (CDCl3) δ 7.50 (d, J=8.09, 1H), 6.51-6.44 (m, 2H), 4.98 (br s, 2H), 3.84 (s, 3H), 3.81 (s, 3H), 3.75 (s, 3H).

Workup

  1. customThe solvent is removed under reduced pressure
  2. additionCH2Cl2 is added to the residue
  3. customthe solvent is removed under reduced pressure
  4. customThe resulting oil is purified by chromatography

Sources & evidence

ORD record
ord-3371e903e3b0434a80ff1f157e394df8
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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