Hydrochloric Acid → (S)-3-Amino-4,4,4-trifluoro-1-p-tolyl-3-(4-(6,6,6-trifluorohexyloxy)phenyl)butan-1-one

HRID 1629769Notes

Reaction equation

HRID 1629769 reaction equation
CC([S@@]([NH:7][C@:8]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([F:38])([F:37])[F:36])=[CH:25][CH:24]=1)([CH2:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)[C:9]([F:12])([F:11])[F:10])=O)(C)C.Cl>CO.O1CCOCC1>[NH2:7][C@@:8]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([F:36])([F:37])[F:38])=[CH:25][CH:24]=1)([C:9]([F:12])([F:11])[F:10])[CH2:13][C:14]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)=[O:22]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86685859(S)-2-Methyl-N-((S)-1,1,1-trifluoro-4-oxo-4-p-tolyl-2-(4-(6,6,6-trifluorohexyloxy)phenyl)butan-2-yl)propane-2-sulfinamide

Product 1

HCID 86685860(S)-3-Amino-4,4,4-trifluoro-1-p-tolyl-3-(4-(6,6,6-trifluorohexyloxy)phenyl)butan-1-oneYield 98.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of Intermediate 8D (482 mg, 0.852 mmol) in MeOH (4 mL) was added 4 M HCl (1 mL, 4.00 mmol) in dioxane. The resulting mixture was stirred at rt for 2 h and then concentrated. The residue was taken up in EtOAc, washed with saturated NaHCO3 and brine, dried (MgSO4), filtered and concentrated to afford Intermediate (386 mg, 58%) as a colorless oil, which was used for the subsequent reaction without further purification. LCMS Anal. Calc'd for C23H25F6NO2 461.18, found [M+H] 461.9.

Workup

  1. concentrationconcentrated
  2. washwashed with saturated NaHCO3 and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-85c0b014da624b0bb14311668e6ef991
Source dataset
uspto-grants-2014_07
Patent number
US08791091B2

Reaction notes

Loading…