Hydrochloric Acid → HCID 118045531, compound

HRID 596014Notes

Reaction equation

HRID 596014 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH:24][S@@](C(C)(C)C)=O)[CH2:10][NH:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-:23])=[O:22])(=[O:14])=[O:13])[CH:5]=[C:6]([F:8])[CH:7]=1.Cl.C([O-])([O-])=O.[Na+].[Na+]>CCOCC>[NH2:24][C@@H:9]([C:4]1[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([Br:1])[CH:3]=1)[CH2:10][NH:11][S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22])(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 118046586HCID 118046586, compound

Product 1

HCID 118045531HCID 118045531, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

N—((S)-2-(3-bromo-5-fluorophenyl)-2-((R)-1,1-dimethylethylsulfinamido)ethyl)-2-nitrobenzenesulfonamide (3.55 g, 6.80 mmol) in Et2O (22.65 mL), and HCl (4 M in dioxane) (3.40 mL, 13.59 mmol) was added. The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was neutralized by Na2CO3 solution and extracted by EtOAc. The organic layer was washed with water, dried, filtered off, and concentrated in vacuo providing the crude (S)—N-(2-amino-2-(3-bromo-5-fluorophenyl)ethyl)-2-nitrobenzenesulfonamide, which was used in next step reaction without further purification. LCMS (m/z): 418.2/420.2 (MH+), 0.62 min.

Workup

  1. extractionextracted by EtOAc
  2. washThe organic layer was washed with water
  3. customdried
  4. filtrationfiltered off
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-26ce61f03924421a89cd85c6d1d60f38
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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