Hydrochloric Acid → HCID 58897174, compound

HRID 1993625Notes

Reaction equation

HRID 1993625 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]([NH:30][S@@](C(C)(C)C)=O)([C:16]2[CH:21]=[C:20]([O:22][C:23]([F:28])([F:27])[CH:24]([F:26])[F:25])[CH:19]=[C:18]([F:29])[CH:17]=2)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[O:37][CH3:38].Cl>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]([C:16]2[CH:21]=[C:20]([O:22][C:23]([F:27])([F:28])[CH:24]([F:26])[F:25])[CH:19]=[C:18]([F:29])[CH:17]=2)([NH2:30])[CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:4][C:3]=1[O:37][CH3:38]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59458649HCID 59458649, compound

Product 1

HCID 58897174HCID 58897174, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-N-((S)-1-(4-fluoro-3-methoxyphenyl)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-phenylethyl)-2-methylpropane-2-sulfinamide (1.1 g, 2 mmol) in MeOH (50 mL) was added 4N HCl (2.5 mL). The reaction mixture was stirred at room temperature for 20 minutes. The organic solvent was removed under reduced pressure. To the residue was added saturated NaHCO3, and the aqueous portion was extracted with ether. The separated organic portion was dried over MgSO4, filtered and concentrated. The residue was purified by ISCO chromatography (40 g column) using hexanes/EtOAc (0-60%) over 18 min to give (S)-1-(4-fluoro-3-methoxyphenyl)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-phenylethanamine as a colorless oil (540 mg, 59% yield). LCMS: RT=1.74 min, [M+H]−17=439.3 (Phenomenex Luna C18 column, 4.6×30 mm eluting with 10-90% MeOH/H2O over 2 minutes containing 0.1% TFA; 5 mL/min, monitoring at 220 nm).

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. additionTo the residue was added saturated NaHCO3
  3. extractionthe aqueous portion was extracted with ether
  4. dry with materialThe separated organic portion was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by ISCO chromatography (40 g column)
  8. customover 18 min

Sources & evidence

ORD record
ord-f216eafaf1d9445893834ffab26539d5
Source dataset
uspto-grants-2010_01
Patent number
US07652023B2

Reaction notes

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