Sulfamic Acid → HCID 86613503, compound

HRID 495307Notes

Reaction equation

HRID 495307 reaction equation
[OH:1][CH2:2][C@@H:3]1[C@@H:7]([CH2:8][OH:9])[O:6][CH:5]([CH2:10][C:11]2[C:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:13]([OH:18])[CH:14]=[C:15]([OH:17])[CH:16]=2)[O:4]1.[Cl:25]([O-])=O.[Na+].S(=O)(=O)(O)N.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1>[OH:1][CH2:2][C@@H:3]1[C@@H:7]([CH2:8][OH:9])[O:6][CH:5]([CH2:10][C:11]2[C:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:13]([OH:18])[CH:14]=[C:15]([OH:17])[C:16]=2[Cl:25])[O:4]1

Participants

7

Reactant 5

HCID 5987Sulfamic AcidHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 23668197Sodium ChloriteHCID 69025681HCID 69025681, compound

Product 1

HCID 86613503HCID 86613503, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 230 (79.6 mg, 0.240 mmol) obtained in Example 230 was dissolved in tetrahydrofuran (10 mL), and sodium chlorite (48.7 mg, 0.538 mmol) and sulfamic acid (102 mg, 1.05 mmol) were added thereto and stirred at room temperature for 2 hours. Aqueous saturated sodium hydrogencarbonate solution and aqueous saturated sodium thiosulfate were added to the reaction solution, and extracted with ethyl acetate. The organic layer was washed with aqueous saturated sodium chloride solution, then dried over anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was purified through preparative thin-layer chromatography (chloroform/methanol/water=100/10/1) to obtain Compound 280 (22.7 mg, 26%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with aqueous saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated away under reduced pressure
  5. customThe resulting residue was purified through preparative thin-layer chromatography (chloroform/methanol/water=100/10/1)

Sources & evidence

ORD record
ord-1f8db2bd186640a9b4f642e9f484270e
Source dataset
uspto-grants-2009_05
Patent number
US07538241B2

Reaction notes

Loading…