Hydrochloric Acid → HCID 86682389, compound

HRID 1748273Notes

Reaction equation

HRID 1748273 reaction equation
I([O-])(=O)(=O)=O.[Na+].[CH3:7][C@@H:8]1[O:13][S:12](=[O:14])[N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][CH2:9]1.Cl.CC[O:25]C(C)=O>C(#N)C.O>[CH3:7][C@@H:8]1[O:13][S:12](=[O:25])(=[O:14])[N:11]([C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[CH2:10][CH2:9]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 23667635Sodium periodateHCID 67235126HCID 67235126, compound

Product 1

HCID 86682389HCID 86682389, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Sodium periodate (341 g, 1.6 mol) is added to a solution of tert-butyl (6S)-6-methyl-1,2,3-oxathiazinane-3-carboxylate 2-oxide (250 g, 1062 mmol) in acetonitrile (2.5 L) and water (1.5 L) at 0° C. The pH of the mixture is adjusted to 7 by the addition of saturated Na2HPO4 solution. A solution of RuCl33H2O (2.20 g, 10.62 mmol) is added at 5° C. and the pH of mixture is kept at 7 by addition of saturated Na2HPO4 solution. The reaction is stirred at room temperature for 2 h. Water is added and pH is adjusted to 6 by addition of 2.0 M HCl solution. EtOAc (1.0 L) is added and the aqueous layer is separated and extracted with EtOAc (2×500 mL). The organic layers are combined, washed with saturated NaHCO3 solution and brine, dried (Na2SO4) and concentrated to afford the crude compound which is purified by flash column chromatography using EtOAc in hexane to afford the title compound (140 g, 52%) as a pale yellow oil.

Workup

  1. additionA solution of RuCl33H2O (2.20 g, 10.62 mmol) is added at 5° C.
  2. customthe aqueous layer is separated
  3. extractionextracted with EtOAc (2×500 mL)
  4. washwashed with saturated NaHCO3 solution and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto afford the crude compound which
  8. customis purified by flash column chromatography

Sources & evidence

ORD record
ord-fb3a90d994e440348b141fec4e65bd1a
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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