HCID 19084820, compound → HCID 19084823, compound

HRID 962401Notes

Reaction equation

HRID 962401 reaction equation
[C:1]([CH2:3][CH2:4][C:5]([OH:13])([P:9]([OH:12])([OH:11])=[O:10])[C:6]([OH:8])=[O:7])#[N:2].[H][H]>N.[Rh]>[NH2:2][CH2:1][CH2:3][CH2:4][C:5]([OH:13])([P:9]([OH:12])([OH:11])=[O:10])[C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 19084820HCID 19084820, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19084823HCID 19084823, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 222AmmoniaSolvent

Procedure

The hydrogenation of 4-cyano-2-hydroxy-2-phosphonobutanoic acid is carried out using the hydrogenation technique of Freifelder (J. Am. Chem. Soc., 8, 2386 (1960)). The cyano compound (2.09 g; 0.01 mole) is placed in 20 ml of 10% methanolic ammonia. Rhodium on alumina (5%) catalyst (0.5 g) is added, and the mixture is hydrogenated at 40 PSI on a Parr apparatus for several hours (until uptake of hydrogen is complete). The catalyst is filtered off, and the filtrate is evaporated dry. The residue treated with cation exchange resin in H+ form to convert the material to acid form. The solution containing it is evaporated to dryness under vacuum. The product is purified by dissolving the residue in water, adding ethanol to give a precipitate, and collecting the solids by filtration. Further purification is accomplished by again recrystallizing from water/ethanol.

Workup

  1. waitthe mixture is hydrogenated at 40 PSI on a Parr apparatus for several hours
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. customdry
  5. additionThe residue treated with cation exchange resin in H+ form
  6. additionThe solution containing it
  7. customis evaporated to dryness under vacuum
  8. customThe product is purified
  9. dissolutionby dissolving the residue in water
  10. additionadding ethanol
  11. customto give a precipitate
  12. customcollecting the solids
  13. filtrationby filtration
  14. customFurther purification
  15. customby again recrystallizing from water/ethanol

Sources & evidence

ORD record
ord-200648140464462792587f4e7eb4ff8f
Source dataset
uspto-grants-1998_06
Patent number
US05760021

Reaction notes

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