Sodium hydride → HCID 69935360, compound

HRID 875020Notes

Reaction equation

HRID 875020 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 69935360HCID 69935360, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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)+

Workup

  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

Sources & evidence

ORD record
ord-f09f4eb70b4e496bad4fec365367d602
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

Loading…