Sodium hydride → HCID 69935360, 화합물

HRID 875020노트

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HRID 875020 반응식
[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

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 86673539HCID 86673539, 화합물

생성물 1

HCID 69935360HCID 69935360, 화합물수율 54.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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)+

후처리

  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

출처 및 근거

ORD 기록
ord-f09f4eb70b4e496bad4fec365367d602
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08981084B2

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