Sodium → 4(R)-nicotinoylthio-3(S)-[1(R)t-butyldimethylsilyloxyethyl]azetidin-2-one

HRID 1609162Notes

Reaction equation

HRID 1609162 reaction equation
C(O[C@H:5]1[NH:8][C:7](=[O:9])[C@@H:6]1[C@H:10]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH3:11])(=O)C.[Na].[C:21]([OH:29])(=[S:28])[C:22]1[CH:27]=[CH:26][CH:25]=[N:24][CH:23]=1>O1CCOCC1.C(OCC)(=O)C.O.[Cl-].[Zn+2].[Cl-]>[C:21]([S:28][C@H:5]1[NH:8][C:7](=[O:9])[C@@H:6]1[C@H:10]([O:12][Si:13]([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:14])[CH3:15])[CH3:11])(=[O:29])[C:22]1[CH:27]=[CH:26][CH:25]=[N:24][CH:23]=1

Participants

8

Reactant 3

HCID 5360545SodiumHCID 10935078AzetidonHCID 178526139HCID 178526139, compound

Product 1

HCID 145381274(R)-nicotinoylthio-3(S)-[1(R)t-butyldimethylsilyloxyethyl]azetidin-2-oneYield 52%

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-(R)acetoxy-3(R)-[1(R)t-butyldimethylsilyloxyethyl]azetidin-2-one (2.87 g) in dioxane (40 ml), the sodium salt of thionicotinic acid (1.94 g) was added. Zinc chloride (1.7 g) was added to the resulting mixture and the reaction mixture was stirred for 4 hours at room temperature. The reaction mixture was then cooled at room temperature and poured in a mixture of ethyl acetate and water. The organic layer was separated, washed twice with water, dried over anhydrous sodium sulphate, and evaporated in vacuo. The residue was purified by column chromatography to give 1.9 g of the title product (52% yield).

Workup

  1. temperatureThe reaction mixture was then cooled at room temperature
  2. customThe organic layer was separated
  3. washwashed twice with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-0568604714a94238943fed9602d1e93c
Source dataset
uspto-grants-1995_03
Patent number
US05399679

Reaction notes

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