Hydrochloric Acid → (2S,4R)-4-amino-4-(6-bromo-3-fluoropyridin-2-yl)-1,1,1,5,5-pentafluoropentan-2-ol

HRID 930359Notes

Reaction equation

HRID 930359 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C@@:8]([NH:19][S@@](C(C)(C)C)=O)([CH2:12][C@@H:13]([OH:18])[C:14]([F:17])([F:16])[F:15])[CH:9]([F:11])[F:10])[C:5]([F:26])=[CH:4][CH:3]=1.Cl>O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+]>[NH2:19][C@:8]([C:6]1[C:5]([F:26])=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=1)([CH:9]([F:11])[F:10])[CH2:12][C@H:13]([OH:18])[C:14]([F:15])([F:16])[F:17]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86732179(R)-N-((2S,4R)-2-(6-bromo-3-fluoropyridin-2-yl)-1,1,5,5,5-pentafluoro-4-hydroxypentan-2-yl)-2-methylpropane-2-sulfinamide

Product 1

HCID 86732180(2S,4R)-4-amino-4-(6-bromo-3-fluoropyridin-2-yl)-1,1,1,5,5-pentafluoropentan-2-ol

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a suspension of (R)-N-((2S,4R)-2-(6-bromo-3-fluoropyridin-2-yl)-1,1,5,5,5-pentafluoro-4-hydroxypentan-2-yl)-2-methylpropane-2-sulfinamide (28 mg, 0.059 mmol) in 1,4-dioxane (396 μl) was added hydrochloric acid, 4 M solution in dioxane (59.4 μl, 0.238 mmol) dropwise. The reaction mixture was stirred at RT for 1 h. The mixture was diluted with saturated Na2CO3 and extracted with EtOAc. The organic layer was washed with brine, and dried over sodium sulfate and concentrated in vacuo. The crude product was obtained as yellow oil. MS m/z=367, 369 M+, Calculated for C10H9BrF6N2O: 367.09.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2052dfbc42194fd39361d19301ba3a2f
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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