Sodium Thiosulfate → HCID 86730303, compound

HRID 1053969Notes

Reaction equation

HRID 1053969 reaction equation
[OH:1][CH:2]1[CH2:6]S[CH2:4][C:3]1([CH3:9])[C:7]#[N:8].C1C=C(Cl)C=C(C(OO)=O)C=1.[S:21]([O-:25])([O-])(=[O:23])=S.[Na+].[Na+]>C(Cl)Cl>[OH:1][CH:2]1[CH2:6][S:21](=[O:25])(=[O:23])[CH2:4][C:3]1([CH3:9])[C:7]#[N:8]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 86730304HCID 86730304, compound

Product 1

HCID 86730303HCID 86730303, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3R,4S and 3S,4R)-4-Hydroxy-3-methyltetrahydrothiophene-3-carbonitrile (140 mg, 0.98 mmol) was dissolved in DCM (4.9 mL) and was stirred vigorously at ambient temperature. m-CPBA (340 mg, 2.0 mmol) was added in three portions and the resulting mixture was maintained at ambient temperature for 18 hours. The mixture was then diluted with 1M aqueous sodium thiosulfate and extracted with EtOAc. The organic layer was again washed with 1M aqueous sodium thiosulfate, saturated aqueous NaHCO3, brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was purified by MPLC on silica gel (using a gradient elution of 0-100% EtOAc/hexanes) to afford the title compound. 1H NMR (600 MHz, CD3OD): δ 4.40 (t, J=6.5 Hz, 1H); 3.70 (d, J=13.6 Hz, 1H); 3.56 (dd, J=13.8, 6.2 Hz, 1H); 3.29-3.30 (m, 1H); 3.23 (dd, J=13.7, 6.8 Hz, 1H); 1.60 (s, 3H).

Workup

  1. temperaturethe resulting mixture was maintained at ambient temperature for 18 hours
  2. extractionextracted with EtOAc
  3. washThe organic layer was again washed with 1M aqueous sodium thiosulfate, saturated aqueous NaHCO3, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by MPLC on silica gel (
  8. washa gradient elution of 0-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7742c7dd64754b669d90dc3c5bcf9062
Source dataset
uspto-grants-2016_07
Patent number
US09394282B2

Reaction notes

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