Diethyl (5-{[(tert-butoxycarbonyl)amino](phenyl)methyl}pyridin-2-yl)phosphonate → Diethyl {5-[amino(phenyl)methyl]pyridin-2-yl}phosphonate

HRID 1525218Notes

Reaction equation

HRID 1525218 reaction equation
C(OC([NH:8][CH:9]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:10]1[CH:11]=[CH:12][C:13]([P:16](=[O:23])([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])=[N:14][CH:15]=1)=O)(C)(C)C>Cl.O1CCOCC1>[NH2:8][CH:9]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:10]1[CH:11]=[CH:12][C:13]([P:16](=[O:23])([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])=[N:14][CH:15]=1

Participants

3

Reactant 1

HCID 131733137Diethyl (5-{[(tert-butoxycarbonyl)amino](phenyl)methyl}pyridin-2-yl)phosphonate

Product 1

HCID 131733139Diethyl {5-[amino(phenyl)methyl]pyridin-2-yl}phosphonateYield 58%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A solution of compound 4-f in HCl/dioxane (100 ml) was stirred at room temperature overnight. The mixture was then concentrated under vacuum and the residue was diluted with water followed by extraction with ethyl acetate. The aqueous layer was basified with ammonia and then extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated to provide the product, 4-g, (1.5 g, 58%). 1H NMR (CD3OD, 300 MHz,): δ 8.64 (s, 1H), 7.77 (m, 2H), 7.22 (m, 5H), 5.16 (s, 1H), 4.07 (m, 4H), 1.22 (m, 6H). (M+H)+=321.

Workup

  1. concentrationThe mixture was then concentrated under vacuum
  2. additionthe residue was diluted with water
  3. extractionfollowed by extraction with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-940d908b91f44fe6bfffce7bd0bd0fa1
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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