Beta-Alanine → Pamidronic Acid

반응식

[P:1]([OH:4])([OH:3])[OH:2].[NH2:5][CH2:6][CH2:7][C:8]([OH:10])=O.N1CCOCC1.P(Cl)(Cl)Cl>>[CH2:7]([C:8]([P:1]([OH:4])([OH:3])=[O:2])([P:1]([OH:4])([OH:3])=[O:2])[OH:10])[CH2:6][NH2:5]

참가 물질

반응물 4

HCID 239Beta-Alanine

HCID 8083Morpholine

HCID 24387Phosphorus trichloride

HCID 107909Phosphorous acid

생성물 1

HCID 4674Pamidronic Acid

반응 조건

온도: 70 °C

실험 절차

The mixture of 5 eq. phosphorous acid and β-alanine is heated to form a melt. Morpholine (1 eq.) is slowly added. The reaction is cooled to about 70° C. and 2 eq. of PCl3 are added. The mixture is heated for about 3.5 hours. Then the reaction is hydrolyzed in aqueous acid at about 75° C. for about 0.5 hours. Crystallization from aqueous acid/IPA, affords pamidronate.