Water → HCID 118492100, compound

HRID 711334Notes

Reaction equation

HRID 711334 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH:6]=O.[CH3:17][C:18]([S@@:21]([NH2:23])=[O:22])([CH3:20])[CH3:19].O>C(Cl)Cl>[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH:6]=[N:23][S@:21]([C:18]([CH3:20])([CH3:19])[CH3:17])=[O:22]

Participants

5

Reactant 3

HCID 962WaterHCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 118492100HCID 118492100, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3,5-bis(trifluoromethyl)benzaldehyde (5 g, 20.7 mmol) and (S)-2-methylpropane-2-sulfinamide (3 g, 24.8 mmol) in DCM (50 ml) at 0° C., was drop wise added Ti(O-iPr)4 (5.9 g, 24.8 mmol) under N2 atmosphere. After stirring for 20 h at room temperature, the reaction mixture was poured into water (100 mL) with vigorous stirring. The precipitate was filtered and the filtrate was extracted with DCM (2×150 mL). The combined organic layers were washed with brine (80 mL), dried over anhydrous MgSO4, and then concentrated. The residue was purified by silica gel chromatography (PE/EtOAc=5/1 to 2/1) to give the title compound (6 g, yield: 84%); m/z (ES+): 346 [M+H]+.

Workup

  1. filtrationThe precipitate was filtered
  2. extractionthe filtrate was extracted with DCM (2×150 mL)
  3. washThe combined organic layers were washed with brine (80 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (PE/EtOAc=5/1 to 2/1)

Sources & evidence

ORD record
ord-90941fd3917d4a049af0ae8fb968e981
Source dataset
uspto-grants-2015_11
Patent number
US09181259B2

Reaction notes

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