2-Nitrobenzenesulfonyl chloride → HCID 118046052, compound

HRID 596013Notes

Reaction equation

HRID 596013 reaction equation
[NH2:1][CH2:2][C@@H:3]([NH:12][S@:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14])[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([Br:11])[CH:5]=1.[N+:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[S:28](Cl)(=[O:30])=[O:29])([O-:21])=[O:20]>C(Cl)Cl>[Br:11][C:6]1[CH:5]=[C:4]([C@H:3]([NH:12][S@:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14])[CH2:2][NH:1][S:28]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N+:19]([O-:21])=[O:20])(=[O:29])=[O:30])[CH:9]=[C:8]([F:10])[CH:7]=1

Participants

4

Reactant 2

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 118045232HCID 118045232, compound

Product 1

HCID 118046052HCID 118046052, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)—N—((S)-2-amino-1-(3-bromo-5-fluorophenyl)ethyl)-2-methylpropane-2-sulfinamide (3.3 g, 9.78 mmol) was dissolved in DCM (32.6 mL) at 0° C., then TEA (1.405 mL, 10.08 mmol), and 2-nitrobenzene-1-sulfonyl chloride (2.169 g, 9.78 mmol) were added. The reaction mixture was stirred at room temperature for 3 h. The reaction mixture was concentrated in vacuo and the crude product was purified to yield N—((S)-2-(3-bromo-5-fluorophenyl)-2-((S)-1,1-dimethylethylsulfinamido)ethyl)-2-nitrobenzenesulfonamide. LCMS (m/z): 522.1/524.1 (MH+), 0.94 min.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe crude product was purified

Sources & evidence

ORD record
ord-9262b6aa63bf44d7b723d3b30dd7f4c1
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

Loading…