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

HRID 1948078Notes

Reaction equation

HRID 1948078 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N:16](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=[CH:12][N:11]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[ClH:31]>CCOC(C)=O>[ClH:31].[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][N:11]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

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, 6H), 3.64 (d, J=22.0 Hz 2H), 3.97-4.04 (m, 4H), 7.50 (dd, J=2.0, 8.8 Hz, 1H), 7.64 (dd, J=2.0, 8.8 Hz, 1H), 7.95 (d, J=2.4 Hz, 1H).

Workup

  1. filtrationThe solids were collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-83da88b79cff4d1e9ec2c1d13384c363
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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