Hydrochloric Acid → HCID 86682391, compound

HRID 1748278Notes

Reaction equation

HRID 1748278 reaction equation
[CH3:1][C@H:2]1[O:7][S:6](=[O:8])[N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4][CH2:3]1.I([O-])(=O)(=O)=[O:17].[Na+].Cl.CCOC(C)=O>C(#N)C.O>[CH3:1][C@H:2]1[O:7][S:6](=[O:17])(=[O:8])[N:5]([C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 23667635Sodium periodateHCID 67234851HCID 67234851, compound

Product 1

HCID 86682391HCID 86682391, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6342AcetonitrileSolvent

Procedure

To a solution of tert-butyl (6R)-6-methyl-1,2,3-oxathiazinane-3-carboxylate 2-oxide (2.3 g, 9.6 mmol) in acetonitrile (25 mL) and water (15 mL) cooled to 0° C. is added sodium periodate (3.1 g, 14.3 mmol) in one portion. After 5 min, the pH of the mixture is adjusted to 7-8 by addition of saturated Na2HPO4 solution. A solution of RuCl3 (9.9 mg, 0.05 mmol) in water (0.5 mL) is added and the reaction mixture is stirred for 2 h, keeping the pH between 6 and 9 by addition of Na2HPO4 solution. Water (100 mL) is added and the pH is adjusted to 6 by addition of 2M HCl solution. EtOAc is added and the organic layer is separated, washed with NaHCO3 and brine. The combined aqueous layers are back extracted once with EtOAc. The combined organic phases are dried (MgSO4) and concentrated to afford the crude compound which is purified by flash column chromatography using EtOAc in hexanes affords the title compound (1.13 g, 47%).

Workup

  1. customthe organic layer is separated
  2. washwashed with NaHCO3 and brine
  3. extractionThe combined aqueous layers are back extracted once with EtOAc
  4. dry with materialThe combined organic phases are dried (MgSO4)
  5. concentrationconcentrated
  6. customto afford the crude compound which
  7. customis purified by flash column chromatography

Sources & evidence

ORD record
ord-20c42527d91c4c5f887d56075c11fac7
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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