N-(t-butoxycarbonylsulfamoyl)-N-(7-benzyloxy-3-methoxy-2-oxo-2H-chromen-6-yl)glycine methyl ester → N-sulfamoyl-N-(7-benzyloxy-3-methoxy-2-oxo-2H-chromen-6-yl)glycine methyl ester
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:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[O:12][C:11](=[O:24])[C:10]([O:25][CH3:26])=[CH:9]2>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH3:1][O:2][C:3](=[O:38])[CH2:4][N:5]([S:27](=[O:37])(=[O:36])[NH2:28])[C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[O:12][C:11](=[O:24])[C:10]([O:25][CH3:26])=[CH:9]2Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of N-(t-butoxycarbonylsulfamoyl)-N-(7-benzyloxy-3-methoxy-2-oxo-2H-chromen-6-yl)glycine methyl ester (0.550 g, 1 mmol) in 40 mL of CH2Cl2/TFA (3:1) is stirred for 40 min at ambient temperature. The solvent is removed under reduced pressure. Methylene chloride is added to the residue and the solvent removed under reduced pressure (4×). The residue is purified by flash chromatography using CH2Cl2/EtOAc (4:1) to afford N-sulfamoyl-N-(7-benzyloxy-3-methoxy-2-oxo-2H-chromen-6-yl)glycine methyl ester as a white solid: mp=178-179° C.; 1H NMR (DMSO-d6) δ 7.74 (s, 1H), 7.52-7.32 (m, 5H), 7.29 (s, 1H), 7.13 (s, 1H), 5.22 (s, 2H), 4.30 (s, 2H), 3.80 (s, 3H), 3.58 (s, 3H); (M−H)−=447.
Workup
- customThe solvent is removed under reduced pressure
- additionMethylene chloride is added to the residue
- customthe solvent removed under reduced pressure (4×)
- customThe residue is purified by flash chromatography
Sources & evidence
- ORD record
- ord-84781176ac284c31b665a8dc784e34c8
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07700633B2
Reaction notes
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