Hydrochloric Acid → HCID 53487253, compound

HRID 220739Notes

Reaction equation

HRID 220739 reaction equation
CC(S([NH:7][C@H:8]([C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1)[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O)(C)C.[ClH:27]>CO.O1CCOCC1>[ClH:27].[C:11]1([CH2:10][CH2:9][C@H:8]([NH2:7])[C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:25])([F:26])[F:24])=[CH:19][CH:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67362728HCID 67362728, compound

Product 1

HCID 53487253HCID 53487253, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

2-methyl-N-{(1S)-3-phenyl-1-[4-(trifluoromethyl)phenyl]propyl}propane-2-sulfinamide (JACS, 2005, 127, 1092-3) (8.3 g, 21.7 mmol) was dissolved in methanol (50 mL) and a 4M solution of HCl in dioxane (10.8 mL) was added. The solution was stirred at RT for 1 h then concentrated. The residue was triturated with isohexane to give a colourless solid which was collected by filtration. 1H NMR (400 MHz), δ (ppm) (DMSO-D6): 8.7 (3H, s), 7.85 (2H, d, J 8.3 Hz), 7.77 ((2H, d, J 8.3 Hz), 7.29-7.26 (2H, m), 7.20-7.13 (3H, m), 4.36 (1H, m), 2.4-2.35 (2H, m), 2.35-2.25 (m, 1H), 2.2-2.1 (1H, m).

Workup

  1. concentrationthen concentrated
  2. customThe residue was triturated with isohexane
  3. customto give a colourless solid which
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-43ed73d5db4449368ed4537772be1dd9
Source dataset
uspto-grants-2012_06
Patent number
US08203004B2

Reaction notes

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