tert-Butylsulfinamide, (S)-(-)- → HCID 59627227, compound

HRID 1523242Notes

Reaction equation

HRID 1523242 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]([CH2:15][CH2:16][C:17]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=O)[C:11](=[O:14])[O:12][CH3:13])[CH3:9])=[CH:4][CH:3]=1.[CH3:26][C:27]([S@@:30]([NH2:32])=[O:31])([CH3:29])[CH3:28]>C1COCC1.[Cl-].[Na+].O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]([CH2:15][CH2:16]/[C:17](=[N:32]/[S@:30]([C:27]([CH3:29])([CH3:28])[CH3:26])=[O:31])/[C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:11](=[O:14])[O:12][CH3:13])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 59627220HCID 59627220, compound

Product 1

HCID 59627227HCID 59627227, compoundYield 77.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (S)-methyl 1-(4-bromophenyl)ethyl(3-(4-fluorophenyl)-3-oxopropyl)carbamate (982 mg, 2 mmol) and (S)-2-methylpropane-2-sulfinamide (265 mg, 2 mmol) in anhydrous THF (20 mL) at rt was added Ti(OEt)4 (1 g, 4 mmol). The reaction mixture was heated at 70° C. for 24 h. After cooling to rt, the reaction mixture was poured into brine with vigorous stirring. The resulting suspension was filtered through a pad of celite and the solid was washed with brine. The combined organic phases were dried, filtered and concentrated to give methyl (1S)-1-(4-bromophenyl)ethyl((Z)-3-((S)-tert-butylsulfinylimino)-3-(4-fluorophenyl)propyl)carbamate (794 mg, 65%). 1H NMR (CD3OD): 1.24 (m, 9H), 1.58 (d, 4H), 1.61 (m, 1H), 2.95 (m, 1H), 3.48 (m, 2H), 3.66 (m, 1H), 3.80 (m, 3H), 4.58 (m, 1H), 3.78 (m, 3H), 5.36 (m, 1H), 7.18 (m, 3H), 7.30 (m, 2H), 7.50 (m, 2H), 7.96 (m, 2H).

Workup

  1. temperatureAfter cooling to rt
  2. filtrationThe resulting suspension was filtered through a pad of celite
  3. washthe solid was washed with brine
  4. customThe combined organic phases were dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-38be6b02d2f64e48aa34fea820d65575
Source dataset
uspto-grants-2015_07
Patent number
US09079861B2

Reaction notes

Loading…