Hydrochloric Acid → HCID 86732106, compound

HRID 930278Notes

Reaction equation

HRID 930278 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:25])=[C:6]([C@@:8]([NH:18][S@@](C(C)(C)C)=O)([CH2:11][C@H:12]([OH:17])[C:13]([F:16])([F:15])[F:14])[CH2:9][F:10])[CH:7]=1.CO.Cl>C(Cl)Cl>[NH2:18][C@@:8]([C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[F:25])([CH2:9][F:10])[CH2:11][C@H:12]([OH:17])[C:13]([F:15])([F:16])[F:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 86732107HCID 86732107, compound

Product 1

HCID 86732106HCID 86732106, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)—N-((2S,4S)-2-(5-bromo-2-fluorophenyl)-1,5,5,5-tetrafluoro-4-hydroxypentan-2-yl)-2-methylpropane-2-sulfinamide (1.6 g, 3.54 mmol, step 6) in DCM (20 mL)/MeOH (10 mL) was added HCl (4.0M in dioxane; 1.075 ml, 35.4 mmol, Aldrich) at RT. The reaction was stirred for one hour. The reaction was concentrated under reduced pressure and the crude residue was taken up in EtOAc. The solution was washed sequentially with water, saturated aqueous sodium bicarbonate solution, and brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to afford the title compound as yellow oil, used without further purification. MS m/z=347.9 M+. Calculated for C11H11BrF5NO: 348.11

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. washThe solution was washed sequentially with water, saturated aqueous sodium bicarbonate solution, and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6f91a971e66649a8b3df3cdddb1a0099
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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