Sodium Sulfite → HCID 18782029, compound

HRID 1420533Notes

Reaction equation

HRID 1420533 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([S:18][CH:19]1[N:22]([CH2:23][C:24](=[O:33])[CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21](=[O:34])[CH2:20]1)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C(=O)([O-])O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>ClCCl.CCOCC>[CH2:12]([S:18]([CH:19]1[N:22]([CH2:23][C:24](=[O:33])[CH2:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:21](=[O:34])[CH2:20]1)=[O:9])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

7

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 18781978HCID 18781978, compound

Product 1

HCID 18782029HCID 18782029, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of m-chloroperbenzoic acid (2.48 g, 0.0144 mol) in dichloromethane (50 ml) was added dropwise to a stirred solution of 4-hexylthio-1-(4-phenyl-2-oxobutyl)azetidin-2-one (4.0 g, 0.012 mol) in dichloromethane (50 ml) at -60° C. Stirring was continued at -60° C. for 30 minutes then the mixture was poured into an aqueous solution of sodium hydrogen carbonate and sodium sulphite. The layers were separated and the aqueous was extracted with dichloromethane. The combined extracts were dried (MgSO4) and evaporated to give a solid which was slurried in ether, filtered, washed with ether and petrol. The solid was recrystallised from ethyl acetate to give the title compound as white crystals, 920 mg, (22%), m.p. 154-5° C.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous was extracted with dichloromethane
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. customevaporated
  5. customto give a solid which
  6. filtrationfiltered
  7. washwashed with ether and petrol
  8. customThe solid was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-a994b0c277e3457a89be9445f7d6efa8
Source dataset
uspto-grants-2000_06
Patent number
US06071899

Reaction notes

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