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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
ノート
印刷プレビュー

反応式

HRID 225972 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 1049PyridineHCID 682631,1'-CarbonyldiimidazoleHCID 34743873,N-Dihydroxy-propionamidineHCID 131727525[(2S,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino)pyrrolidin-2-yl] acetic acid2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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%

後処理

  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)

出典と根拠

ORDレコード
ord-b5b549cd351c45be97dd0f0cba5438f3
出典データセット
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07557136B2

反応ノート

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