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Pyridine → (3Ez,5s)-1-(biphenyl-4-ylcarbonyl)-5-{[3-(2-hydroxyethyl)-1,2,4-oxadiazol-5-yl]methyl}pyrrolidin-3-one o-methyloxime

HRID 225972
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HRID 225972 반응식
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][C:4]([C:7]([N:9]2[CH2:13][C:12](=[N:14][O:15][CH3:16])[CH2:11][C@H:10]2[CH2:17][C:18](O)=[O:19])=[O:8])=[CH:3][CH:2]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.O[N:40]=[C:41]([NH2:45])[CH2:42][CH2:43][OH:44].N1C=CC=CC=1>O1CCCC1>[CH3:16][O:15][N:14]=[C:12]1[CH2:11][C@@H:10]([CH2:17][C:18]2[O:19][N:45]=[C:41]([CH2:42][CH2:43][OH:44])[N:40]=2)[N:9]([C:7]([C:4]2[CH:5]=[CH:6][C:1]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:2][CH:3]=2)=[O:8])[CH2:13]1
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참가 물질

6

반응물 4

HCID 1049PyridineHCID 682631,1'-CarbonyldiimidazoleHCID 34743873,N-Dihydroxy-propionamidineHCID 131727525[(2S,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino)pyrrolidin-2-yl] acetic acid2회

생성물 1

HCID 131727535(3Ez,5s)-1-(biphenyl-4-ylcarbonyl)-5-{[3-(2-hydroxyethyl)-1,2,4-oxadiazol-5-yl]methyl}pyrrolidin-3-one o-methyloxime수율 32.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of [(2S,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino)pyrrolidin-2-yl]acetic acid (Intermediate 7, 50 mg, 0.14 mmol) in tetrahydrofuran (2 ml) was added CDI (37 mg, 0.23 mmol). The reaction mixture was stirred 1 h30. A solution of N′,3-dihydroxypropanimidamide (16 mg, 0.16 mmol), pyridine (34 ml, 0.14 mmol) in tetrahydrofuran was then added and the reaction mixture was stirred at reflux overnight The solvent was removed and ethyl acetate was added. The organic phase was washed with citric acid 5%, NH4Cl, NaHCO3 then brine. The organic phase was dried (MgSO4), concentrated and purified on silica gel column chromatography (Ethyl acetate) to afford (3EZ,5S)-1-(biphenyl-4-ylcarbonyl)-5-{[3-(2-hydroxyethyl)-1,2,4-oxadiazol-5-yl]methyl}pyrrolidin-3-one O-methyloxime (19 mg). Yield: 27%. HPLC purity: 94%

후처리

  1. stirringthe reaction mixture was stirred
  2. temperatureat reflux overnight The solvent
  3. customwas removed
  4. additionethyl acetate was added
  5. washThe organic phase was washed with citric acid 5%, NH4Cl, NaHCO3
  6. dry with materialThe organic phase was dried (MgSO4)
  7. concentrationconcentrated
  8. custompurified on silica gel column chromatography (Ethyl acetate)

출처 및 근거

ORD 기록
ord-b5b549cd351c45be97dd0f0cba5438f3
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07557136B2

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