Hydrochloric Acid → HCID 57948940, compound

HRID 1992282Notes

Reaction equation

HRID 1992282 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@@:9]([NH:15][S@@](C(C)(C)C)=O)([CH2:11][C:12]([CH3:14])=[CH2:13])[CH3:10])[CH:5]=[CH:6][C:7]=1[F:8].Cl>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([C@@:9]([NH2:15])([CH2:11][C:12]([CH3:14])=[CH2:13])[CH3:10])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57948929HCID 57948929, compound

Product 1

HCID 57948940HCID 57948940, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (R)-N-((S)-2-(3-bromo-4-fluorophenyl)-4-methylpent-4-en-2-yl)-2-methylpropane-2-sulfinamide (1.8 g, 5.1 mmoles, 1 equiv) in 1,4-dioxane (6 mL) is added hydrogen chloride (4.0 M in 1,4-dioxane, 15 mL). The reaction is stirred for 5 minutes and the solvent is removed under reduced pressure. To the residue is added saturated aqueous sodium bicarbonate and the mixture is extracted with ethyl acetate. The combined organic phase is dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (97% yield): 1H NMR (CDCl3, 400 MHz) δ 7.66 (dd, 1H, J=6.40, J=2.80 Hz), 7.37-7.33 (m, 1H), 7.02 (t, 1H, J=8.40 Hz), 4.83 (s, 1H), 4.62 (s, 1H), 2.47 (d, 1H, J=13.2 Hz), 2.35 (d, 1H, J=13.2 Hz), 1.44 (s, 3H), 1.36 (s, 3H).

Workup

  1. customthe solvent is removed under reduced pressure
  2. additionTo the residue is added saturated aqueous sodium bicarbonate
  3. extractionthe mixture is extracted with ethyl acetate
  4. dry with materialThe combined organic phase is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-25da6ff8ece14165b626dae3a9d2a1ed
Source dataset
uspto-grants-2010_01
Patent number
US07648983B2

Reaction notes

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