Sodium → HCID 54270161, compound

HRID 1609161Notes

Reaction equation

HRID 1609161 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:24])(=[S:23])[CH3:22]>O1CCOCC1.C(OCC)(=O)C.O.[Br-].[Zn+2].[Br-]>[C:21]([S:23][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:24])[CH3:22]

Participants

8

Reactant 3

HCID 5360545SodiumHCID 10935078AzetidonHCID 178418634HCID 178418634, compound

Product 1

HCID 54270161HCID 54270161, compoundYield 89.1%

Reagents, catalysts & solvents 4

HCID 10421208Zinc bromideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

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 thioacetic acid (1.2 g) was added. Zinc bromide (2.7 g) was added to the resulting suspension and the reaction mixture was stirred for 4 hours at 40° C. 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 sulfate, and evaporated in vacuo. The residue was purified by column chromatography to give 2.7 g of the title product (89% 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 sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-9b4a28c99b1444e39d2f44663a58173e
Source dataset
uspto-grants-1995_03
Patent number
US05399679

Reaction notes

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