Pyridine → HCID 86680224, compound

HRID 1428778Notes

Reaction equation

HRID 1428778 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][NH:7][S:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:27]1([O:33][C:34](Cl)=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O1CCCC1.C(#N)C>[C:27]1([O:33][C:34](=[O:35])[NH:1][C:2]2[CH:20]=[CH:19][C:5]([CH2:6][NH:7][S:8](=[O:10])(=[O:9])[NH:11][C:12]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:18])=[CH:4][CH:3]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 86679393HCID 86679393, compound

Product 1

HCID 86680224HCID 86680224, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 22177404Acetonitrile tetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl N-(4-aminobenzyl)sulfamoylcarbamate (86 mg, 0.285 mmol) was dissolved in a tetrahydrofuran/acetonitrile (1:1 mixture). Pyridine (0.03 mL, 0.342 mmol) was added, followed by addition of phenylchloroformate (0.04 mL, 0.3 mmol) at 0° C. The mixture was stirred at 0° C. for 30 min and further 30 min at room temperature. The reaction mixture was extracted with ethyl acetate and washed with brine. Drying over magnesium sulfate, evaporation of the ethyl acetate and purification by column chromatography gave the N-[4-[[(tert-butoxycarbonyl-sulfamoyl)amino]methyl]-phenyl]-carbamic acid phenyl ester (59 mg, 49%).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialDrying over magnesium sulfate, evaporation of the ethyl acetate and purification by column chromatography

Sources & evidence

ORD record
ord-ad84edfc71cf41569b700f4c35f8fa62
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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