Triethylamine → (5-(4-Chlorophenyl)-1,3,4-oxadiazol-2-yl)(3-hydroxyazetidin-1-yl)methanone

HRID 1639501노트

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HRID 1639501 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]([O:15]CC)=O)=[N:10][N:9]=2)=[CH:4][CH:3]=1.[C-]#N.[Na+].Cl.[OH:22][CH:23]1[CH2:26][NH:25][CH2:24]1.C(N(CC)CC)C>CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][C:11]([C:13]([N:25]3[CH2:26][CH:23]([OH:22])[CH2:24]3)=[O:15])=[N:10][N:9]=2)=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 8929Sodium CyanideHCID 27592903-Hydroxyazetidine hydrochlorideHCID 46742983Ethyl 5-(4-chlorophenyl)-1,3,4-oxadiazole-2-carboxylate

생성물 1

HCID 59563510(5-(4-Chlorophenyl)-1,3,4-oxadiazol-2-yl)(3-hydroxyazetidin-1-yl)methanone수율 90%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 962Water용매

실험 절차

To a suspension of ethyl 5-(4-chlorophenyl)-1,3,4-oxadiazole-2-carboxylate—for preparation, see e.g. WO 97/05131—(0.53 g, 2.10 mmol) in dry methanol (10 mL) was added sodium cyanide (20 mg, 0.42 mmol). A solution of 3-hydroxyazetidine hydrochloride (0.38 g, 2.78 mmol) and triethylamine (0.39 mL, 2.78 mmol) in methanol (10 mL) was added at ambient temperature. The mixture was stirred for 2.5 h. Water (30 mL) was added and the mixture was extracted with dichloromethane. The organic layers were combined and evaporated to a white solid, which was treated with toluene (5 mL) and then filtered. The product was washed with toluene (5 mL) and then dried in vacuo. There was obtained 0.52 g (90%) of 2B as a solid. 1H NMR (400 MHz, CD3OD): δ 4.00 (dd, 1H), 4.46 (dd, 2H), 4.70 (m, 1H), 4.93 (dd, 1H), 7.62 (d, 2H), 8.11 (d, 2H), MS (APCI+) m/z 280 [M+H]+.

후처리

  1. customfor preparation
  2. extractionthe mixture was extracted with dichloromethane
  3. customevaporated to a white solid, which
  4. additionwas treated with toluene (5 mL)
  5. filtrationfiltered
  6. washThe product was washed with toluene (5 mL)
  7. customdried in vacuo

출처 및 근거

ORD 기록
ord-bb1d1108f0ec4bee80f3b58e069b1af9
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08110566B2

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