Potassium → HCID 9907013, compound

HRID 1609159Notes

Reaction equation

HRID 1609159 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.[K].[C:21]([O:24][CH2:25][C:26]([OH:28])=[S:27])(=[O:23])[NH2:22]>O1CCOCC1.C(OCC)(=O)C.O.[Br-].[Zn+2].[Br-]>[C:21]([O:24][CH2:25][C:26]([S:27][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:28])(=[O:23])[NH2:22]

Participants

8

Reactant 3

HCID 5462222PotassiumHCID 10935078AzetidonHCID 178514124HCID 178514124, compound

Product 1

HCID 9907013HCID 9907013, compoundYield 90.1%

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 potassium salt of carbamoyloxythioacetic acid (2.1 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 solid residue was taken-up with CH2Cl2. Upon addition of hexanes and cooling a white solid was precipitated, and collected by filtration to give 3.26 g of the title product (90% 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. additionUpon addition of hexanes
  7. temperaturecooling a white solid
  8. customwas precipitated
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-5ea93d28b46e46058a89eebc0f95ef09
Source dataset
uspto-grants-1995_03
Patent number
US05399679

Reaction notes

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