p-Toluenesulfonic acid → HCID 86652635, compound

HRID 2092714Notes

Reaction equation

HRID 2092714 reaction equation
[F:1][C:2]([F:26])([F:25])[C@@H:3]([CH3:24])[O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:22][CH2:21][C:13]3([CH2:20][CH2:19][C:16]4([O:18][CH2:17]4)[CH2:15][CH2:14]3)[C:12]2=[O:23])=[CH:7][CH:6]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)(Cl)Cl.C(OCC)(=O)C>[O:23]=[C:12]1[C:13]2([CH2:14][CH2:15][CH:16]([CH:17]=[O:18])[CH2:19][CH2:20]2)[CH2:21][CH2:22][N:11]1[C:8]1[CH:7]=[CH:6][C:5]([O:4][C@H:3]([CH3:24])[C:2]([F:25])([F:1])[F:26])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 58229934HCID 58229934, compound

Product 1

HCID 86652635HCID 86652635, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8-[4-((R)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-1-oxa-8-aza-dispiro[2.2.4.2]dodecan-7-one (50 mg, 135 umol, obtained in example 252, Step 2) in chloroform was added tosic acid (26 mg, 135 umol) and the reaction mixture was stirred overnight at room temperature and then diluted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to give a crude residue which was purified by flash column chromatography (grad 0% to 80% EtOAc in heptane) to yield the title compound as a white solid (7 mg, 14%). MS (m/e): 370.1 (MH+).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a crude residue which
  6. customwas purified by flash column chromatography (grad 0% to 80% EtOAc in heptane)

Sources & evidence

ORD record
ord-4cbd39bcc5134553b6ab9b15d7453159
Source dataset
uspto-grants-2013_05
Patent number
US08440710B2

Reaction notes

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