N,N-Dimethylglycine hydrochloride → Methyl 3-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)-5-(1-methyl-2-oxopyrrolidin-3-yloxy)benzoate

HRID 75964

반응식

HRID 75964 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH:13]2[CH2:17][CH2:16][N:15]([CH3:18])[C:14]2=[O:19])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Cl.CN(C)CC(O)=O.I[C:29]1[CH:34]=[CH:33][C:32]([C:35]2[O:36][C:37]([CH3:40])=[N:38][N:39]=2)=[CH:31][CH:30]=1>O1CCOCC1.[Cu](I)I>[CH3:40][C:37]1[O:36][C:35]([C:32]2[CH:31]=[CH:30][C:29]([O:1][C:2]3[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH:13]4[CH2:17][CH2:16][N:15]([CH3:18])[C:14]4=[O:19])[CH:11]=3)[C:5]([O:7][CH3:8])=[O:6])=[CH:34][CH:33]=2)=[N:39][N:38]=1

참가 물질

6

반응물 3

HCID 75605N,N-Dimethylglycine hydrochlorideHCID 6765692-(4-Iodophenyl)-5-methyl-[1,3,4]oxadiazole2회HCID 66971906Methyl 3-hydroxy-5-(1-methyl-2-oxopyrrolidin-3-yloxy)benzoate2회

생성물 1

HCID 66972059Methyl 3-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)-5-(1-methyl-2-oxopyrrolidin-3-yloxy)benzoate수율 30.7%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 312751,4-Dioxane용매

실험 절차

To a stirred mixture of Methyl 3-hydroxy-5-(1-methyl-2-oxopyrrolidin-3-yloxy)benzoate (15 g) (Intermediate 3), N,N-dimethylglycine hydrochloride (2.3 g), copper (II) iodide (1 g) in dry 1,4-dioxane was added 2-(4-iodophenyl)-5-methyl-1,3,4-oxadiazole (15.4 g) (Intermediate 4) under nitrogen. The reaction mixture was refluxed for 24 h. The reaction mixture was cooled, quenched with water and extracted with DCM. Combined organic washings were washed with water, brine, dried over Na2SO4, filtered and concentrated in vacuo to get the crude product. The crude product was purified by column chromatography using silica gel as stationary phase and ethyl acetate: petroleum ether (9:1) as mobile phase to give the product (7 g) as thick liquid.

후처리

  1. temperatureThe reaction mixture was refluxed for 24 h
  2. temperatureThe reaction mixture was cooled
  3. customquenched with water
  4. extractionextracted with DCM
  5. washCombined organic washings were washed with water, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto get the crude product
  10. customThe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-5e29f283917d45e2a7c3fd3018e4b0ee
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835469B2

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