3-Cyano-1-diethoxyphosphinylpropanesulfonic acid lithium salt → 4-Amino-1-phosphonobutanesulfonic acid

HRID 2696

반응식

HRID 2696 반응식
[Li+].[C:2]([CH2:4][CH2:5][CH:6]([P:11]([O:16]CC)([O:13]CC)=[O:12])[S:7]([O-:10])(=[O:9])=[O:8])#[N:3].[H][H]>N.[Rh]>[NH2:3][CH2:2][CH2:4][CH2:5][CH:6]([P:11]([OH:16])([OH:13])=[O:12])[S:7]([OH:10])(=[O:8])=[O:9]

참가 물질

5

반응물 2

HCID 883520073-Cyano-1-diethoxyphosphinylpropanesulfonic acid lithium saltHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 189360834-Amino-1-phosphonobutanesulfonic acid

시약·촉매·용매 2

HCID 23948Rhodium촉매HCID 222Ammonia용매

실험 절차

The hydrogenation of 3-cyano-1-diethoxyphosphinylpropanesulfonic acid lithium salt is carried out using the hydrogenation technique of Freifelder (J. Am. Chem. Soc., 82, 2386 (1960)). The cyano compound (2.62 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 product is hydrolyzed by dissolving the residue in 25 ml of 6N HCl and refluxing the solution for 12-24 hours. It is then evaporated to dryness under vacuum on a rotary evaporator. Distilled water (25 ml) is added, and the solution is again evaporated dry. The resulting residue is dissolved in a few ml H2O, and ethanol is added to precipitate a solid. This is recrystallized from water/ethanol to yield 4-amino-1-phosphonobutanesulfonic acid.

후처리

  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. dissolutionby dissolving the residue in 25 ml of 6N HCl
  6. temperaturerefluxing the solution for 12-24 hours
  7. customIt is then evaporated to dryness under vacuum on a rotary evaporator
  8. additionDistilled water (25 ml) is added
  9. customthe solution is again evaporated
  10. customdry
  11. dissolutionThe resulting residue is dissolved in a few ml H2O, and ethanol
  12. additionis added
  13. customto precipitate a solid
  14. customThis is recrystallized from water/ethanol

출처 및 근거

ORD 기록
ord-5f1b002fa6a34530a6058c7ef3ffccff
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731299

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