Sodium Thiosulfate → HCID 89813764, compound

HRID 525326Notes

Reaction equation

HRID 525326 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH:24]1[CH2:29][CH2:28][CH:27]([N:30]2[C@@H:34]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:33]([CH3:42])([CH3:41])[O:32][C:31]2=[O:43])[CH2:26][CH2:25]1.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:41][C:33]1([CH3:42])[O:32][C:31](=[O:43])[N:30]([CH:27]2[CH2:26][CH2:25][C:24](=[O:23])[CH2:29][CH2:28]2)[C@H:34]1[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 89813649HCID 89813649, compound

Product 1

HCID 89813764HCID 89813764, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (500 mL, 0.3 M in DCM, 0.15 mol) was added over 15 minutes to an ice-cooled solution of (S)-3-(4-hydroxycyclohexyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (39.5 g, 0.136 mol) in DCM (1 L). The resulting mixture was stirred at room temperature under nitrogen for 22.5 hours. Saturated aqueous Na2S2O3 (300 mL) and saturated aqueous NaHCO3 (300 mL) were added, and the mixture was stirred at room temperature for 1 hour. The organic layer was separated, washed with brine (300 mL), dried, filtered and concentrated. The resulting residue was purified by column chromatography (eluting with 100% DCM to DCM/MeOH=100:1) to afford (S)-5,5-dimethyl-3-(4-oxocyclohexyl)-4-phenyloxazolidin-2-one (25 g, 64%). 1H NMR (300 MHz, d6-DMSO) δ ppm 7.45-7.20 (m, 5H), 4.67 (s, 1H), 4.0-3.90 (m, 1H), 2.60-2.35 (m, 2H), 2.25-1.95 (m, 4H), 1.85-1.70 (m, 1H), 1.55-1.40 (m, 1H), 1.47 (s, 3H), 0.80 (s, 3H). m/z (ESI) 288 (M+H)+.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. customThe organic layer was separated
  3. washwashed with brine (300 mL)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by column chromatography (eluting with 100% DCM to DCM/MeOH=100:1)

Sources & evidence

ORD record
ord-e0e9acb761db464c86ee90f65d37fe98
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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