Hydrochloric Acid → HCID 86732166, compound

HRID 930347Notes

Reaction equation

HRID 930347 reaction equation
[Br:1][C:2]1[N:7]=[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])[C:5]([F:25])=[CH:4][CH:3]=1.Cl.C([O-])(O)=O.[Na+]>O1CCOCC1>[NH2:18][C@@:8]([C:6]1[C:5]([F:25])=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=1)([CH2:9][F:10])[CH2:11][C@H:12]([OH:17])[C:13]([F:15])([F:14])[F:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86732167HCID 86732167, compound

Product 1

HCID 86732166HCID 86732166, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a 150 mL round-bottomed flask was added (R)-N-((2S,4S)-2-(6-bromo-3-fluoropyridin-2-yl)-1,5,5,5-tetrafluoro-4-hydroxypentan-2-yl)-2-methylpropane-2-sulfinamide (2.01 g, 4.43 mmol), 1,4-dioxane (30 mL) and finally HCl in 1,4-dioxane (Aldrich; 4.43 mL, 17.7 mmol, 4 M). The solution was stirred at rt for 45 min and then poured into sat NaHCO3 (100 mL) and extracted with EtOAc (2×100 mL). The combined extracts were dried (Na2SO4) and concentrated to afford (2S,4S)-4-amino-4-(6-bromo-3-fluoropyridin-2-yl)-1,1,1,5-tetrafluoropentan-2-ol which was carried on directly. MS m/z=351.0 [M+H]+. Calculated for C10H10BrF5N2O: 350.0.

Workup

  1. additionpoured
  2. extractionextracted with EtOAc (2×100 mL)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-14128f1de2f04f139461287115161210
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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