Pyridine → HCID 178444033, compound

HRID 582183Notes

Reaction equation

HRID 582183 reaction equation
Cl.[NH2:2][OH:3].N1C=CC=CC=1.[PH:10](=[O:13])([OH:12])[OH:11].[CH2:14]([C:16]([CH2:44][CH3:45])([C:18](=O)[C:19]1[N:23]=[CH:22][N:21]([C:24]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:20]=1)[CH3:17])[CH3:15]>C(O)C>[PH:10](=[O:11])([OH:13])[OH:12].[CH2:14]([C:16]([CH2:44][CH3:45])([C:18](=[N:2][OH:3])[C:19]1[N:23]=[CH:22][N:21]([C:24]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:20]=1)[CH3:17])[CH3:15]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 178444074HCID 178444074, compound

Product 1

HCID 178444033HCID 178444033, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine hydrochloride (0.29 g), then pyridine (7.7 ml), was added under nitrogen to a stirred solution of diethyl 3-oxo-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (1.0 g, prepared as described in Example 42) in ethanol (20 ml). The mixture was stirred at room temperature for three hours, then evaporated under reduced pressure. The residue was treated with water, basified to pH 8 with 1M sodium hydroxide solution, and extracted with chloroform. The organic layers were washed with brine, dried over magnesium sulphate and evaporated under reduced pressure. The residue was chromatographed on silica, using dichloromethane-ethanol (19:1) as eluant, to give diethyl 3-oximino-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (0.90 g, m.p. 190-192° C.), probably as a single geometric isomer of unknown configuration. NMR (CDCl3): δ 1.2(6H,t), 1.95-2.1(2H,m), 3.05(2H,m), 3.95(4H,m), 7.1-7.3(15H,m), 8.0(1H,s), 9.1(1H,br).

Workup

  1. customevaporated under reduced pressure
  2. additionThe residue was treated with water
  3. extractionextracted with chloroform
  4. washThe organic layers were washed with brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated under reduced pressure
  7. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-f6f92a3f7eed40a28f07ef02e4e618f9
Source dataset
uspto-grants-1999_07
Patent number
US05922644

Reaction notes

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