Dichloromethane → HCID 178465716, compound

HRID 2404182Notes

Reaction equation

HRID 2404182 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[C:17]([C:22](=O)[CH3:23])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:25][C:26]([S@@:29]([NH2:31])=[O:30])([CH3:28])[CH3:27].C(Cl)Cl>[Cl-].[Na+].O>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[C:17](/[C:22](=[N:31]\[S@@:29]([C:26]([CH3:28])([CH3:27])[CH3:25])=[O:30])/[CH3:23])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 66926615HCID 66926615, compound

Product 1

HCID 178465716HCID 178465716, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To the solution of 1-[6-(4-tert-Butyl-cyclohexyloxy)-quinolin-2-yl]-ethanone (0.2227 g, 0.0006843 mol) and (s)-(−)-2-Methyl-2-propanesulfinamide (0.0829 g, 0.000684 mol) in Methylene chloride (1.4 mL, 0.021 mol) was added Ti(OEt)4 (0.488 mL, 0.00171 mol). The reaction was stirred at room temperature for id. The mixture was then cooled to 0° C., added equal volume brine, filtrate through celite, and extracted with EtOAc. After died over Na2SO4, the residue was chromatographed 0-50% EA/HE gave product (132 mg, 45%). LCMS 2.39 min m/z 429.30 ([M+1], 100%).

Workup

  1. temperatureThe mixture was then cooled to 0° C.
  2. extractionextracted with EtOAc
  3. customthe residue was chromatographed 0-50% EA/HE

Sources & evidence

ORD record
ord-1684c8c4078741beba6e2b2d6c7c8644
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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