Hydrochloric Acid → HCID 59458399, compound

HRID 238817Notes

Reaction equation

HRID 238817 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@:12]([NH:34][S@@](C(C)(C)C)=O)([C:20]2[CH:25]=[C:24]([O:26][C:27]([F:32])([F:31])[CH:28]([F:30])[F:29])[CH:23]=[C:22]([F:33])[CH:21]=2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].Cl>CO.CCOCC>[F:1][C:2]1[CH:3]=[C:4]([C@:12]([C:20]2[CH:25]=[C:24]([O:26][C:27]([F:31])([F:32])[CH:28]([F:29])[F:30])[CH:23]=[C:22]([F:33])[CH:21]=2)([NH2:34])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59458362HCID 59458362, compound

Product 1

HCID 59458399HCID 59458399, compoundYield 101.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of (R)—N—((R)-1-(3-fluoro-4-isopropoxyphenyl)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-phenylethyl)-2-methylpropane-2-sulfinamide (398 mg, 0.678 mmol) in MeOH (1.5 mL) was added HCl (1.5 mL, 4 M solution in dioxane) and the reaction mixture was stirred for 30 min. The reaction mixture was diluted with ether (50 mL) and the organic layer was washed with sat. NaHCO3 (20 mL), dried over Na2SO4, filtered and concentrated to give (R)-1-(3-fluoro-4-isopropoxyphenyl)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-phenylethanamine as a colorless oil (334 mg, 100% yield). LCMS: RT=1.76 min [M−NH2] 467.24 (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); HPLC: RT=3.04 min, Purity 95% (Phenomenex Luna C18 column, 4.6×50 mm eluting with 10-90% MeOH/H2O over 4 minutes containing 0.2% PPA; 4 mL/min, monitoring at 220 nm) NMR: 400 MHz 1H (CDCl3) 7.15 ppm, 3H, m; 6.99 ppm, 4H, m; 6.89 ppm, 1H, m; 6.84 ppm, 1H, d, J=8.79 Hz; 6.74 ppm, 2H, d, J=6.15 Hz; 5.87 ppm, 1H, m; 4.42 ppm, 1H, m; 3.47 ppm, 2H, s; 1.27 ppm, 6H, dd, J=7.91, 6.15 Hz.

Workup

  1. washthe organic layer was washed with sat. NaHCO3 (20 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-55013bb202d942b6a412c006ad6c4fbc
Source dataset
uspto-grants-2014_02
Patent number
US08642576B2

Reaction notes

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