Sodium hydride → L-Ornithine, 2-(difluoromethyl)-, monohydrochloride

HRID 890850

반응식

HRID 890850 반응식
[H-].[Na+].[CH2:3]([CH2:13][NH2:14])[CH2:4][C:5]([NH2:12])([C:9]([OH:11])=[O:10])[CH:6]([F:8])[F:7].O.[ClH:16]>C1COCC1>[OH2:10].[ClH:16].[F:7][CH:6]([F:8])[C@@:5]([C:9]([OH:11])=[O:10])([CH2:4][CH2:3][CH2:13][NH2:14])[NH2:12]

참가 물질

4

반응물 2

HCID 24758Sodium hydrideHCID 441361Ornithine, 2-(difluoromethyl)-, hydrochloride, hydrate (1:1:1)

생성물 1

HCID 23393214L-Ornithine, 2-(difluoromethyl)-, monohydrochloride

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

Into a dry 100 ml three necked RB flask equipped with a stirrer, gas inlet and outlet arrangement methyl-2,5-di[1-(3,4-chlorophenyl) methylidene amino] pentanoate (2.0 g) and sodium hydride (0.21 g) in dry THF (20 ml) were added. The resulting suspension was stirred at 50° C. under a nitrogen atmosphere for 2 hrs. The reaction mixture was then cooled to 5° C. and the nitrogen inlet was replaced with chlorodifluoromethane gas tube. The gas was passed for about 45 mts. The reaction was stirred at RT and allowed to stand overnight. The reaction mixture was worked up by quenching with water and the pH was adjusted to 2 with aqueous HCl. The reaction mixture was extracted with MDC twice. The water layer was concentrated and taken up in methanol and chilled. The crystallized inorganic material was removed. The filtrate was concentrated and the residue taken up in 6N HCl and hydrolyzed. The resulting aqueous layer was evaporated. The crude product was dissolved in ethanol, chilled again to remove any inorganic material and further purified by water-acetone to give a product with a melting point (mp) 223–225° C. with spectral data such as NMR matching with material obtained in Example 8.

후처리

  1. additionwere added
  2. temperatureThe reaction mixture was then cooled to 5° C.
  3. customthe nitrogen inlet was replaced with chlorodifluoromethane gas tube
  4. stirringThe reaction was stirred at RT
  5. waitto stand overnight
  6. customby quenching with water
  7. extractionThe reaction mixture was extracted with MDC twice
  8. concentrationThe water layer was concentrated
  9. temperaturechilled
  10. customThe crystallized inorganic material was removed
  11. concentrationThe filtrate was concentrated
  12. customThe resulting aqueous layer was evaporated
  13. dissolutionThe crude product was dissolved in ethanol
  14. temperaturechilled again
  15. customto remove any inorganic material
  16. customfurther purified by water-acetone
  17. customto give a product with a melting point (mp) 223–225° C. with spectral data such as NMR

출처 및 근거

ORD 기록
ord-8abbce2adf624bb59fa89840c8920f77
출처 데이터셋
uspto-grants-2006_02
특허 번호
US06998502B1

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