Ethylmorpholine → 1-ethyl-5-oxo-N-[(2,3,4-trifluorophenyl)methyl]-prolinamide

HRID 554080노트

반응식

HRID 554080 반응식
[CH2:1]([N:3]1[C:10](=[O:11])[CH2:9][CH2:8][C@H:4]1[C:5]([OH:7])=O)[CH3:2].ON1C2C=CC=CC=2N=N1.[F:22][C:23]1[C:28]([F:29])=[C:27]([F:30])[CH:26]=[CH:25][C:24]=1[CH2:31][NH2:32].C(N1CCOCC1)C.Cl.CN(C)CCCN=C=NCC>ClCCl.Cl.CN(C)C=O>[CH2:1]([N:3]1[C:10](=[O:11])[CH2:9][CH2:8][C@H:4]1[C:5]([NH:32][CH2:31][C:24]1[CH:25]=[CH:26][C:27]([F:30])=[C:28]([F:29])[C:23]=1[F:22])=[O:7])[CH3:2]

참가 물질

9

반응물 5

HCID 7525EthylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27770422,3,4-Trifluorobenzylamine2회HCID 18605196L-Proline, 1-ethyl-5-oxo-

생성물 1

HCID 674618211-ethyl-5-oxo-N-[(2,3,4-trifluorophenyl)methyl]-prolinamide수율 33.3%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

1-Ethyl-5-oxo-proline (0.050 g, 0.32 mmol) was dissolved in anhydrous dichloromethane (˜7 ml) and dimethylformamide (1 ml) and to this was added 1-hydroxybenzotriazole (0.052 g, 0.38 mmol), [(2,3,4-trifluorophenyl)methyl]amine (0.103 g, 0.64 mmol), N-ethyl morpholine (0.151 ml, 0.95 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.073 g, 0.38 mmol). The mixture was shaken at room temperature over the weekend. A further aliquot of [(2,3,4-trifluorophenyl)methyl]amine (0.051 g, 0.32 mmol) was added to the mixture and stirring continued for a while longer until HPLC indicated that no further product was forming. The mixture was diluted with 2M aqueous hydrogen chloride (5 ml) and then filtered through a phase separator. The organic layer was then washed with saturated aqueous sodium hydrogen carbonate and again filtered through a phase separator. The organic layer was then evaporated to give the crude product. The crude material was purified by mass-directed automated HPLC to give pure 1-ethyl-5-oxo-N-[(2,3,4-trifluorophenyl)methyl]-prolinamide (0.032 g).

후처리

  1. stirringstirring
  2. customwas forming
  3. filtrationfiltered through a phase separator
  4. washThe organic layer was then washed with saturated aqueous sodium hydrogen carbonate
  5. filtrationagain filtered through a phase separator
  6. customThe organic layer was then evaporated
  7. customto give the crude product
  8. customThe crude material was purified

출처 및 근거

ORD 기록
ord-32bd4605d9704d5db573d2d9d2b76e4b
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08048907B2

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