Gamma-Aminobutyric Acid → Alendronic Acid

HRID 412674

Reaction equation

HRID 412674 reaction equation
[P:1]([OH:4])([OH:3])[OH:2].[NH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=O.P(Cl)(Cl)Cl>>[CH2:7]([CH2:6][NH2:5])[CH2:8][C:9]([P:1]([OH:4])([OH:3])=[O:2])([P:1]([OH:4])([OH:3])=[O:2])[OH:11]

Participants

4

Reactant 3

HCID 119Gamma-Aminobutyric AcidHCID 24387Phosphorus trichlorideHCID 107909Phosphorous acid

Product 1

HCID 2088Alendronic Acid

Conditions

Temperature
70 °C

Procedure

The mixture of 5 eq. phosphorous acid, 4-aminobutyric acid and morpholine. HCl is melted together until uniform solution is formed. The reaction mixture is cooled to about 70° C. and 2 eq. of PCl3 are carefully added. The mixture is heated for about 5.5 hours before the reaction mixture is hydrolyzed in aqueous acid at about 80° C. and alendronate is isolated from an ethanolic solution.

Workup

  1. customis formed
  2. temperatureThe mixture is heated for about 5.5 hours before the reaction mixture
  3. customis hydrolyzed in aqueous acid at about 80° C.

Sources & evidence

ORD record
ord-b3a0f7fd2bd7403f9357ce99aee0cb71
Source dataset
uspto-grants-2003_05
Patent number
US06562974B2

Linked notes

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