tert-butyl N-(2-fluoro-4-nitrobenzyl)sulfamoylcarbamate → tert-butyl N-(4-amino-2-fluorobenzyl)sulfamoylcarbamate

HRID 1428787Notes

Reaction equation

HRID 1428787 reaction equation
[F:1][C:2]1[CH:20]=[C:19]([N+:21]([O-])=O)[CH:18]=[CH:17][C:3]=1[CH2:4][NH:5][S:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:8])=[O:7]>C(O)C.O1CCCC1.[Pd]>[NH2:21][C:19]1[CH:18]=[CH:17][C:3]([CH2:4][NH:5][S:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:8])=[O:7])=[C:2]([F:1])[CH:20]=1

Participants

5

Reactant 1

HCID 86679394tert-butyl N-(2-fluoro-4-nitrobenzyl)sulfamoylcarbamate

Product 1

HCID 86680228tert-butyl N-(4-amino-2-fluorobenzyl)sulfamoylcarbamateYield 102.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

10% Pd/C (42 mg) was added to a solution of tert-butyl N-(2-fluoro-4-nitrobenzyl)sulfamoylcarbamate (135 mg) in ethanol and tetrahydrofuran. The mixture was charged with H2 and stirred for 6 h. The reaction mixture was filtered using celite and evaporated in vacuo to obtain tert-butyl N-(4-amino-2-fluorobenzyl)sulfamoylcarbamate (127 mg, 99%).

Workup

  1. additionThe mixture was charged with H2
  2. filtrationThe reaction mixture was filtered
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-f2026a2f811d409e94ebb55f38fa5fbc
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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