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

HRID 1639501ノート

反応式

HRID 1639501 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 962Water溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-bb1d1108f0ec4bee80f3b58e069b1af9
出典データセット
uspto-grants-2012_02
特許番号
US08110566B2

反応ノート

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