4-(4-Azido-2-methyl-3-oxobutan-2-yl)-2-chlorobenzenesulfonamide → HCID 66740651, compound

HRID 83872Notes

Reaction equation

HRID 83872 reaction equation
[N:1]([CH2:4][C:5](=[O:20])[C:6]([C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH2:18])(=[O:17])=[O:16])=[C:11]([Cl:19])[CH:10]=1)([CH3:8])[CH3:7])=[N+]=[N-]>CCO.Cl.O=[Pt]=O>[ClH:19].[NH2:1][CH2:4][C:5](=[O:20])[C:6]([C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH2:18])(=[O:17])=[O:16])=[C:11]([Cl:19])[CH:10]=1)([CH3:8])[CH3:7]

Participants

5

Reactant 1

HCID 866622504-(4-Azido-2-methyl-3-oxobutan-2-yl)-2-chlorobenzenesulfonamide

Product 1

HCID 66740651HCID 66740651, compoundYield 189.2%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A pressure bottle was charged with a solution of 4-(4-azido-2-methyl-3-oxobutan-2-yl)-2-chlorobenzenesulfonamide (8 g, 25.2 mmol) in EtOH (100 mL), conc HCl (20 mL) and PtO2 (114 mg, 0.5 mmol, 0.02 eq) and then was purged with hydrogen (2×45 psi). The bottle was pressurized with hydrogen (45 psi) and agitated 2 h. The reaction mixture was filtered through Celite™ and the filtrate was evaporated. The residue was triturated with Et2O, filtered and dried to afford 4-(4-amino-2-methyl-3-oxobutan-2-yl)-2-chlorobenzenesulfonamide hydrochloride (7.8 g, 94% yield) as yellow solid. 1H NMR (400 MHz, DMSO) δ 8.22 (br s, 3H), 7.91 (d, J=8.4 Hz, 1H), 7.60 (s, 2H), 7.50 (s, 1H), 7.43 (d, J=8.4 Hz, 1H), 3.92 (m, 2H), 1.49 (s, 6H).

Workup

  1. customwas purged with hydrogen (2×45 psi)
  2. filtrationThe reaction mixture was filtered through Celite™
  3. customthe filtrate was evaporated
  4. customThe residue was triturated with Et2O
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-171166ba50ea4b83a25f47154dfd8b85
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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