Sodium Thiosulfate → HCID 68709273, compound

HRID 1696712Notes

Reaction equation

HRID 1696712 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[O:11][C@@H:10]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[C@H:9]([CH3:20])S[C:7]=2[CH:6]=[CH:5][CH:4]=1.[Br-:21].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.[S:54]([O-:58])([O-])(=[O:56])=S.[Na+].[Na+].C(=O)([O-])O.[Na+]>CO.C(Cl)(Cl)Cl>[Br:21][C:17]1[CH:18]=[C:13]([C@H:10]2[C@H:9]([CH3:20])[S:54](=[O:58])(=[O:56])[C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:12]=3[O:11]2)[CH:14]=[CH:15][C:16]=1[OH:19]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 17977687Phenyltrimethylammonium bromide dibromideHCID 59396735HCID 59396735, compound

Product 1

HCID 68709273HCID 68709273, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

4-[(2S*,3S*)-8-methoxy-3-methyl-2,3-dihydro-1,4-benzoxathiin-2-yl]phenol synthesized in Reference Example 14 was dissolved in a mixed solvent of methanol (12 mL) and chloroform (6 mL), and with cooling with ice, a methanol (6 mL) solution of phenyltrimethylammonium tribromide (304 mg) was dropwise added over 5 minutes, and thereafter with cooling with ice, this was stirred for 1.5 hours. Aqueous saturated sodium thiosulfate solution (4 mL) and aqueous saturated sodium hydrogencarbonate solution (4 mL) were added, and then immediately back-extracted twice with chloroform. The organic layer was collected, washed with saturated saline, dried with magnesium sulfate, and the solvent was evaporated off under reduced pressure. The obtained residue was purified by reversed-phase HPLC (0.1% TFA acetonitrile/H2O=10% to 95%, gradient) to obtain the entitled compound (146 mg, 52%) as a white solid.

Workup

  1. temperaturewith cooling with ice
  2. temperaturewith cooling with ice
  3. extractionimmediately back-extracted twice with chloroform
  4. customThe organic layer was collected
  5. washwashed with saturated saline
  6. dry with materialdried with magnesium sulfate
  7. customthe solvent was evaporated off under reduced pressure
  8. customThe obtained residue was purified by reversed-phase HPLC (0.1% TFA acetonitrile/H2O=10% to 95%, gradient)

Sources & evidence

ORD record
ord-7ce080d02b27498aa6fa2670f6a49a3b
Source dataset
uspto-grants-2012_04
Patent number
US08163770B2

Reaction notes

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