Hydrochloric Acid → ethyl 2-((N-(p-methoxybenzyl)sulfamoyl)amino)acetate

HRID 492007Notes

Reaction equation

HRID 492007 reaction equation
Cl.C(OC([N:9]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[S:10]([NH:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:12])=[O:11])=O)CCC>CO>[CH3:28][O:27][C:24]1[CH:23]=[CH:22][C:21]([CH2:20][NH:9][S:10]([NH:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:11])=[O:12])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18449913ethyl 2-((N-(butyloxycarbonyl)-N-(p-methoxybenzyl)sulfamoyl)amino)acetate

Product 1

HCID 18449916ethyl 2-((N-(p-methoxybenzyl)sulfamoyl)amino)acetateYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of HCl in methanol (2 M) was added ethyl 2-((N-(butyloxycarbonyl)-N-(p-methoxybenzyl)sulfamoyl)amino)acetate from the previous step (2.0 g, 5.0 mmol) in portions at RT and the mixture was stirred for 3 h. After the solvent was removed in vacuo, the residue was washed with diethyl ether to afford ethyl 2-((N-(p-methoxybenzyl)sulfamoyl)amino)acetate (1.0 g, 70%). 1H-NMR (DMSO-d6): δ 7.43 (t, J=6.0 Hz, 1H), 7.287 (t, J=6.4 Hz, 1H), 7.21 (d, J=8.4 Hz, 2H), 6.86 (d, J=8.4 Hz, 2H), 3.94 (d, J=4.8 Hz, 2H), 3.71 (s, 3H), 3.64 (d, J=6.0 Hz, 2H), 3.62 (s, 3H),

Workup

  1. customAfter the solvent was removed in vacuo
  2. washthe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-c4715e2d9e194938b61027a3ca8ca8fd
Source dataset
uspto-grants-2009_05
Patent number
US07531566B2

Reaction notes

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