Pyridine → HCID 66762121, compound

HRID 532971Notes

Reaction equation

HRID 532971 reaction equation
C[N:2](C)[C:3](=[N:5][C:6]([CH:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]1)=[S:7])[CH3:4].N1C=CC=CC=1.NOS(O)(=O)=O>C(O)C.CO>[CH3:4][C:3]1[N:5]=[C:6]([CH:8]2[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)[S:7][N:2]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 76284hydroxylamine-O-sulfonic acidHCID 86658793HCID 86658793, compound

Product 1

HCID 66762121HCID 66762121, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Compound 10a (1.5 g, 4.78 mmol) was stirred in ethanol (20 mL) and treated with pyridine (0.76 g, 9.6 mmol). A solution of hydroxylamine-O-sulfonic acid (0.65 g, 5.74 mmol), in methanol (4 mL) was added and stirring continued for 2.5 hours. The mixture was allowed to stand overnight at 4° C. The mixture was condensed under vacuum and extracted with dichloromethane and deionized water. The organic layer was dried (Na2SO4) and condensed under vacuum. The product was filtered through a plug of silica gel, with hexane:EtOAc (8:2) to remove low Rf impurities, and dried to 0.92 g of clear oil. MS (ESI) m/z 322 [M+K]+. 1H NMR (CDCl3) δ 1.47 (s, 9H), 1.59-1.68 (m, 1H), 1.71-1.88 (m, 2H), 2.12-2.22 (m, 1H), 3.02-3.12 (t, 1H), 3.15-3.35 (m, 2H), 3.81-3.90 (dt, 1H), 4.14 (bs, 1H).

Workup

  1. waitto stand overnight at 4° C
  2. customcondensed under vacuum
  3. extractionextracted with dichloromethane
  4. customThe organic layer was dried
  5. custom(Na2SO4) and condensed under vacuum
  6. filtrationThe product was filtered through a plug of silica gel, with hexane:EtOAc (8:2)
  7. customto remove low Rf impurities
  8. dry with materialdried to 0.92 g of clear oil

Sources & evidence

ORD record
ord-0cbab358fa924896bf4d12f5eaf9f1eb
Source dataset
uspto-grants-2014_10
Patent number
US08853219B2

Reaction notes

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