HCID 118045789, compound → HCID 118045232, compound

HRID 596005Notes

Reaction equation

HRID 596005 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH:14][S@:15]([C:17]([CH3:20])([CH3:19])[CH3:18])=[O:16])[CH2:10][N+:11]([O-])=O)[CH:5]=[C:6]([F:8])[CH:7]=1.[H][H]>CO.O=[Pt]=O>[NH2:11][CH2:10][C@@H:9]([NH:14][S@:15]([C:17]([CH3:20])([CH3:19])[CH3:18])=[O:16])[C:4]1[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

5

Reactant 2

HCID 118045789HCID 118045789, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 118045232HCID 118045232, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

(S)—N—((S)-1-(3-bromo-5-fluorophenyl)-2-nitroethyl)-2-methylpropane-2-sulfinamide (2.2 g, 5.99 mmol) was dissolved in MeOH (19.97 mL), flushed with N2 for 10 min, and then PtO2 (0.408 g, 1.797 mmol) was added. The reaction mixture was charged with hydrogen balloon and stirred at room temperature overnight. The reaction mixture was filtered through celite and washed by methanol and EtOAc. The filtrate was dried over Na2SO4, filtered and concentrated. The crude material was used in next step reaction without further purification. LCMS (m/z): 337.1/339.1 (MH+), 0.64 min.

Workup

  1. customflushed with N2 for 10 min
  2. filtrationThe reaction mixture was filtered through celite
  3. washwashed by methanol and EtOAc
  4. dry with materialThe filtrate was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was used in next step reaction without further purification
  8. custom337.1/339.1 (MH+), 0.64 min.

Sources & evidence

ORD record
ord-58d2876ca0bb437fb7cd5286c5238dfa
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

Loading…