Sodium Phosphate, Dibasic → HCID 10276276, compound

HRID 1017283Notes

Reaction equation

HRID 1017283 reaction equation
OOS([O-])=O.[K+].C1(S[C:14]2([O:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][C:19]=3[C@H:29]3[CH2:33][O:32][C@:31]4([CH2:39][CH2:38][C@@H:37]5[NH:40][C@@:34]4([C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[CH2:35][C@H:36]5S(C4C=CC=CC=4)(=O)=O)[CH2:30]3)[CH2:16][CH2:15]2)C=CC=CC=1.[O-2].[Al+3].[O-2].[O-2].[Al+3].P([O-])([O-])(O)=O.[Na+].[Na+]>[Na].[Hg].CO.C(Cl)(Cl)Cl>[CH:14]1([O:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:26])([F:27])[F:28])=[CH:20][C:19]=2[C@H:29]2[CH2:33][O:32][C@:31]3([CH2:39][CH2:38][C@H:37]4[NH:40][C@@:34]3([C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)[CH2:35][CH2:36]4)[CH2:30]2)[CH2:16][CH2:15]1

Participants

8

Reactant 4

HCID 24203Sodium Phosphate, DibasicHCID 9989226AluminaHCID 23707502Potassium hydroxy sulfiteHCID 70152229HCID 70152229, compound

Product 1

HCID 10276276HCID 10276276, compoundYield 61.7%

Reagents, catalysts & solvents 3

HCID 9837419Sodium amalgamCatalystHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

Oxone (400 mg, 0.65 mmol) was added to a stirred mixture of (1R*,2R*,4′S*,5S*,6R*)-2′,3′,4′,5′-tetrahydro-4′-[2-(1-phenylthiocyclopropyloxy)-5-trifluoromethoxyphenyl]-1-phenyl-6-phenylsulphonylspiro[8-azabicyclo[3.2.1]octane-2,2′-furan] (Description 17; 88 mg, 0.12 mmol), wet aluminium oxide (5 g of Al2O3 in 1 ml of water, 370 mg) and chloroform (5 ml) at room temperature. The reaction mixture was stirred for 5 hours then filtered and concentrated to give crude disulphone (95 mg). Sodium amalgam (10%, 700 mg) was added in small portions to the stirred mixture of the disulphone (95 mg), disodium hydrogen orthophosphate (700 mg), and methanol (5 ml) at +5° C. After reaction went to completion, the mixture was quenched with saturated aqueous NaHCO3, decanted and extracted into dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (dichloromethane:methanol) to give the title compound (34 mg, 60%).

Workup

  1. filtrationthen filtered
  2. concentrationconcentrated
  3. customto give crude disulphone (95 mg)
  4. customAfter reaction
  5. customthe mixture was quenched with saturated aqueous NaHCO3
  6. customdecanted
  7. extractionextracted into dichloromethane
  8. dry with materialThe combined organic extracts were dried (Na2SO4)
  9. concentrationconcentrated
  10. customThe residue was purified by chromatography on silica gel (dichloromethane:methanol)

Sources & evidence

ORD record
ord-877f312084564978a92d201c76837ecf
Source dataset
uspto-grants-2002_11
Patent number
US06479486B2

Reaction notes

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