Sodium hydride → HCID 69935360、化合物

HRID 875020ノート

反応式

HRID 875020 の反応式
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([CH:15]=P(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[S:13][CH:14]=2)=[CH:6][CH:5]=1.O=[C:36]1[CH2:39][N:38]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:37]1>C1COCC1>[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12]([CH:15]=[C:36]3[CH2:37][N:38]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:39]3)[S:13][CH:14]=2)=[CH:8][CH:9]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 86673539HCID 86673539、化合物

生成物 1

HCID 69935360HCID 69935360、化合物収率 54.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium hydride (0.818 g, 20.4 mmol) was added to a solution of 4-(4-fluorophenyl)-2-((triphenylphosphoranylidene)methyl)thiazole (3.1 g, 5.84 mmol) in THF (15.0 mL) at 0° C. and the reaction mixture was stirred for 30 min. tert-Butyl 3-oxoazetidine-1-carboxylate (1.0 g, 5.84 mmol) was then added portionwise and the reaction mixture was allowed to warm up to room temperature and stirred overnight. The reaction mixture was then poured over crushed ice and then filtered through Celite. The filtrate was extracted with CH2Cl2. The combined extracts were dried over sodium sulphate and concentrated under reduced pressure to provide tert-butyl 3-((4-(4-fluorophenyl)thiazol-2-yl)methylene)azetidine-1-carboxylate (1.1 g, 10.89%). 1H NMR (400 MHz, CDCl3) δ 7.78-7.82 (m, 2H), 7.30 (s, 1H), 7.02-7.06 (m, 2H), 6.54-6.55 (t, 1H), 4.83-4.85 (t, 2H), 4.61-4.64 (q, 2H), 1.54 (s, 9H). MS (ESI) m/z: Calculated for C18H19FN2O2S: 346.12. found: 347.0 (M+H)+

後処理

  1. additionwas then added portionwise
  2. additionThe reaction mixture was then poured
  3. customover crushed ice
  4. filtrationfiltered through Celite
  5. extractionThe filtrate was extracted with CH2Cl2
  6. dry with materialThe combined extracts were dried over sodium sulphate
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-f09f4eb70b4e496bad4fec365367d602
出典データセット
uspto-grants-2015_03
特許番号
US08981084B2

反応ノート

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