Hydrochloric Acid → Diethyl [(5-aminopyridin-2-yl)methyl]phosphonate hydrochloride

HRID 511510Notes

Reaction equation

HRID 511510 reaction equation
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[CH:10]=[CH:11][C:12]([CH2:15][P:16](=[O:23])([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])=[N:13][CH:14]=1)=O)(C)(C)C.[ClH:31]>CCOC(C)=O>[ClH:31].[NH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][P:16](=[O:23])([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86654051Diethyl ({5-[bis(tert-butoxycarbonyl)amino]pyridin-2-yl}methyl)phosphonate2×

Product 1

HCID 86654049Diethyl [(5-aminopyridin-2-yl)methyl]phosphonate hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of diethyl ({5-[bis(tert-butoxycarbonyl)amino]pyridin-2-yl}methyl)phosphonate (Compound 260B, 2.5 g, 5.6 mmol) in dry EtOAc (150 mL) was added HCl in EtOAc solution dropwise. The reaction mixture was stirred at room temperature for 1 h. The solids were collected by filtration, dried to give 2.1 g of the desired product as a white solid. 1H NMR (DMSO-d6, 400 MHz): δ=1.16 (t, J=7.2 Hz, 6 H), 3.64 (d, J=22.0 Hz 2 H), 3.97-4.04 (m, 4H), 7.50 (dd, J=2.0, 8.8 Hz, 1 H), 7.64 (dd, J=2.0, 8.8 Hz, 1 H), 7.95 (d, J=2.4 Hz, 1 H).

Workup

  1. filtrationThe solids were collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-ab5777725d70427aa9ef7be003d5b365
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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