Hydrochloric Acid → 3-(6-Aminopyridin-3-yl)-2-{[benzyl(hydroxy)phosphoryl]methyl}propanoic acid

HRID 2223240Notes

Reaction equation

HRID 2223240 reaction equation
[CH2:1]([P:8]([CH2:11][CH:12]([CH2:16][C:17]1[CH:18]=[N:19][C:20]([NH:23]C(OC(C)(C)C)=O)=[CH:21][CH:22]=1)[C:13]([OH:15])=[O:14])([OH:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CCOC(C)=O>[NH2:23][C:20]1[N:19]=[CH:18][C:17]([CH2:16][CH:12]([CH2:11][P:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)([OH:10])=[O:9])[C:13]([OH:15])=[O:14])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 688023693-[Benzyl(hydroxy)phosphoryl]-2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)propanoic acid

Product 1

HCID 688016463-(6-Aminopyridin-3-yl)-2-{[benzyl(hydroxy)phosphoryl]methyl}propanoic acidYield 68%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

3-[Benzyl(hydroxy)phosphoryl]-2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)propanoic acid (46 mg; 0.11 mmol) was dissolved in EtOAc (2 mL) and 1 mL of EtOAc, which had been saturated with HCl (g), was added. The reaction was stirred at room temperature overnight. The reaction mixture was concentrated to yield 25 mg (64%) of 3-(6-aminopyridin-3-yl)-2-{[benzyl(hydroxy)phosphoryl]methyl}propanoic acid.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-f2105a79d5a64b07ac7357acce64e281
Source dataset
uspto-grants-2008_05
Patent number
US07375121B2

Reaction notes

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