p-Toluenesulfonic acid monohydrate → (S)-3-{[4-(4-Acetyl-3-hydroxy-2-propyl-phenylsulfanylmethyl)-phenyl]-hydroxy-methyl}-benzonitrile

HRID 1818471Notes

Reaction equation

HRID 1818471 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:13]([C:16]1[CH:21]=[CH:20][C:19]([S:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C@H:30]([O:39]C3CCCCO3)[C:31]3[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=3)[C:34]#[N:35])=[CH:26][CH:25]=2)=[C:18]([CH2:46][CH2:47][CH3:48])[C:17]=1[OH:49])(=[O:15])[CH3:14]>CO>[C:13]([C:16]1[CH:21]=[CH:20][C:19]([S:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([C@H:30]([OH:39])[C:31]3[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=3)[C:34]#[N:35])=[CH:28][CH:29]=2)=[C:18]([CH2:46][CH2:47][CH3:48])[C:17]=1[OH:49])(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 66699467HCID 66699467, compound

Product 1

HCID 66699627(S)-3-{[4-(4-Acetyl-3-hydroxy-2-propyl-phenylsulfanylmethyl)-phenyl]-hydroxy-methyl}-benzonitrileYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add p-toluenesulfonic acid monohydrate (78 mg, 0.41 mmol) to a solution of (S)-3-[[4-(4-Acetyl-3-hydroxy-2-propyl-phenylsulfanylmethyl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile (177 mg, 0.34 mmol) in methanol (5 ml) at room temperature. Stir the mixture for 1.5 hours, concentrate, and dissolve the residue in ethyl acetate (25 ml) and saturated aqueous sodium bicarbonate (35 ml). Wash the organic layer with saturated aqueous sodium bicarbonate, brine, dry over sodium sulfate and concentrate. Purify the crude product via silica chromatography eluting with 1:2 ethyl acetate:hexanes to give the title compound (122 mg, 84%). MS (m/z) 430 (M−H).

Workup

  1. concentrationconcentrate
  2. dissolutiondissolve the residue in ethyl acetate (25 ml)
  3. washWash the organic layer with saturated aqueous sodium bicarbonate, brine
  4. dry with materialdry over sodium sulfate
  5. concentrationconcentrate
  6. customPurify the crude product via silica chromatography
  7. washeluting with 1:2 ethyl acetate

Sources & evidence

ORD record
ord-3d824b2e84414b54978ac566fa7142e7
Source dataset
uspto-grants-2009_10
Patent number
US07598423B2

Reaction notes

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