Sodium Phosphate, Dibasic → HCID 69654642, compound

HRID 1267880Notes

Reaction equation

HRID 1267880 reaction equation
[NH2:1][C@@H:2]1[CH2:8][CH2:7][C@@H:6]2[NH:9][C@@:3]1([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:4][C@H:5]2S(C1C=CC=CC=1)(=O)=O.P([O-])([O-])(O)=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>CO.[Na].[Hg]>[NH2:1][C@@H:2]1[CH2:8][CH2:7][C@@H:6]2[NH:9][C@@:3]1([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:4][CH2:5]2

Participants

6

Reactant 3

HCID 24203Sodium Phosphate, DibasicHCID 516892Sodium BicarbonateHCID 70009050HCID 70009050, compound

Product 1

HCID 69654642HCID 69654642, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 9837419Sodium amalgamCatalystHCID 887MethanolSolvent

Procedure

(1R*,2R*,5S*,6R*)-2-amino-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octane (Description 5; 1.0 g, 2.9 mmol) in methanol (20 mL) was treated with disodium hydrogen phosphate (1.65 g, 11.6 mmol) and 10% sodium amalgam (2.67 g), and the mixture stirred for 40 minutes. Saturated sodium bicarbonate solution (100 mL) was then added and the suspension extracted with dichloromethane (2×100 mL). The extracts were dried (MgSO4) and concentrated, and the residue purified by silica chromatography to give the title compound as a gum (315 mg, 1.6 mmol).

Workup

  1. extractionthe suspension extracted with dichloromethane (2×100 mL)
  2. dry with materialThe extracts were dried (MgSO4)
  3. concentrationconcentrated
  4. customthe residue purified by silica chromatography

Sources & evidence

ORD record
ord-f0da9342cc554bb19354aa1275316336
Source dataset
uspto-grants-2003_04
Patent number
US06555552B2

Reaction notes

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