Ethanol → 3-(3-pentyl)-L-phenylalanine

HRID 369811노트

반응식

HRID 369811 반응식
[O:1]=[C:2]1[C@H:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[CH:10]=2)[NH:6][C@@H](C2C=CC=CC=2)[C@@H](C2C=CC=CC=2)[O:3]1.CCO>Cl[Pd]Cl.C1COCC1>[CH3:19][CH2:18][CH:15]([C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[CH2:8][C@@H:7]([C:2]([OH:3])=[O:1])[NH2:6])[CH2:16][CH3:17]

참가 물질

5

반응물 2

HCID 702EthanolHCID 57269594(2R,3S,5S)-oxo-2,3-diphenyl-5-(3-(3-pentyl)benzyl)morpholine

생성물 1

HCID 206376833-(3-pentyl)-L-phenylalanine수율 84%

시약·촉매·용매 2

HCID 24290Palladium Chloride촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a 300 mL Parr bottle were added 0.41 g of PdCl2, 1.36 g of (2R, 3S, 5S)-6-oxo-2,3-diphenyl-5-(3-(3-pentyl)benzyl)morpholine, 50 mL of EtOH, and 30 mL of THF. The mixture was deoxygenated by bubbling nitrogen through for 10 min and was hydrogenated at 45 psi for 18 h. The vessel was purged with nitrogen, catalyst removed by filtration through celite, and the filtrate concentrated in vacuo to a volume of 15 mL. The solution was chilled in an ice bath and triturated with additional of 50 mL of hexane. A fine precipitate slowly formed. After storing at 5° C. overnight, the solid was collected by filtration and dried in vacuo to afford 0.65 g (72%) of 3-(3-pentyl)-L-phenylalanine.HCl as a white powder, m.p. 170° C. (dec).

후처리

  1. customThe mixture was deoxygenated
  2. customby bubbling nitrogen through for 10 min
  3. customThe vessel was purged with nitrogen, catalyst
  4. customremoved by filtration through celite
  5. concentrationthe filtrate concentrated in vacuo to a volume of 15 mL
  6. temperatureThe solution was chilled in an ice bath
  7. customtriturated with additional of 50 mL of hexane
  8. customA fine precipitate slowly formed
  9. waitAfter storing at 5° C. overnight
  10. filtrationthe solid was collected by filtration
  11. customdried in vacuo

출처 및 근거

ORD 기록
ord-dba9e60ecb8e446aa2010cb0b1633f22
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06140100

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