tert-Butylsulfinamide, (R)-(+)- → HCID 58485262, compound

HRID 2091523Notes

Reaction equation

HRID 2091523 reaction equation
[CH3:1][C:2]([CH3:25])([CH3:24])[C@@H:3]([N:5]([CH2:13][CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)=O)[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4].[CH3:26][C:27]([S@:30]([NH2:32])=[O:31])([CH3:29])[CH3:28]>C1COCC1.[Cl-].[Na+].O>[C:27]([S@:30](/[N:32]=[C:15](/[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)\[CH2:14][CH2:13][N:5]([C@H:3]([C:2]([CH3:25])([CH3:24])[CH3:1])[CH3:4])[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:31])([CH3:29])([CH3:28])[CH3:26]

Participants

5

Reactant 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 58485256HCID 58485256, compound

Product 1

HCID 58485262HCID 58485262, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of (S)-tert-butyl 3,3-dimethylbutan-2-yl(3-(4-fluorophenyl)-3-oxopropyl)carbamate (1.50 g, 4.27 mmol) in dry THF (20 mL) was added Ti(Oi-Prl)4 (2.46 g, 8.55 mmol) and (R)-2-methylpropane-2-sulfinamide (1.03 g, 8.55 mmol) under N2, and the mixture was refluxed overnight. After the reaction was over, the solution was poured into 20 mL brine and filtered. The filtrate was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give the crude product, which was purified by chromatography to afford tert-butyl (E)-3-((R)-tert-butylsulfinylimino)-3-(4-fluorophenyl)propyl((S)-3,3-dimethylbutan-2-yl)carbamate (800 mg, 42%). 1H NMR (CDCl3): 0.75 (s, 9H), 1.26 (m, 12H), 1.47 (s, 8H), 3.27 (m, 2H), 3.49 (m, 2H), 3.91 (m, 1H), 7.14 (m, 2H), 7.89 (m, 1H), 8.25 (m, 1H).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. filtrationfiltered
  3. extractionThe filtrate was extracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product, which
  9. customwas purified by chromatography

Sources & evidence

ORD record
ord-fde851689395467cbd62dcd389e877ab
Source dataset
uspto-grants-2013_05
Patent number
US08440658B2

Reaction notes

Loading…