Tert-Butanesulfinamide → HCID 71280004, compound

HRID 246666Notes

Reaction equation

HRID 246666 reaction equation
O=[C:2]1[CH2:5][CH:4]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:3]1.[CH3:14][C:15]([S:18]([NH2:20])=[O:19])([CH3:17])[CH3:16]>C1COCC1>[C:15]([S:18]([N:20]=[C:2]1[CH2:5][CH:4]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:3]1)=[O:19])([CH3:17])([CH3:16])[CH3:14]

Participants

4

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 23374584tert-Butyl 3-oxocyclobutylcarbamate

Product 1

HCID 71280004HCID 71280004, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of tert-butyl 3-oxocyclobutylcarbamate (2.2 g, 11.9 mmol), 2-methylpropane-2-sulfinamide (1.6 g, 13.1 mmol), Ti(OEt)4 (5.5 g, 24 mmol) in 20 mL of THF was stirred at 50-60° C. overnight. The mixture was cooled to room temperature and then quenched with saturated NH4Cl solution. The formed solid was removed by filtration. The filtrate was evaporated to dryness and the crude residue was purified by silica gel chromatography (200-300 mesh, eluting with a mixture of petroleum ether and ethyl acetate (4:1)) to give tert-butyl 3-(tert-butylsulfinylimino)cyclobutylcarbamate as clear oil (2.0 g, 58%). MS: (M+H)+=289.1; 1H NMR (300 MHz, CDCl3): δ 5.08 (m, 1H), 4.29 (s, 1H), 3.42-3.00 (m, 4H), 1.43 (s, 9H), 1.22 (s, 9H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customquenched with saturated NH4Cl solution
  3. customThe formed solid was removed by filtration
  4. customThe filtrate was evaporated to dryness
  5. customthe crude residue was purified by silica gel chromatography (200-300 mesh
  6. washeluting with a mixture of petroleum ether and ethyl acetate (4:1))

Sources & evidence

ORD record
ord-62b3ce6f881041e9843f39205d838fce
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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