Sodium Sulfite → HCID 18782006, compound

HRID 1420531Notes

Reaction equation

HRID 1420531 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([S:16][CH:17]1[N:20]([CH2:21][C:22](=[O:31])[CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19](=[O:32])[CH2:18]1)[CH2:13][CH2:14][CH3:15].C(=O)([O-])O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>ClCCl.CCOCC>[CH2:12]([S:16]([CH:17]1[N:20]([CH2:21][C:22](=[O:31])[CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19](=[O:32])[CH2:18]1)=[O:9])[CH2:13][CH2:14][CH3:15]

Participants

7

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 18781979HCID 18781979, compound

Product 1

HCID 18782006HCID 18782006, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of m-chloroperbenzoic acid (0.81 g, 0.0047 moles) in dichloromethane (50 ml) was added dropwise to a stirred solution of 4-butylthio-N-(4-phenyl-2-oxobutyl)azetidin-2-one (1.2 g, 0.0039 moles) in dichloromethane (50 ml) at -60° C. Stirring 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 and evaporated to give a solid which was slurried in ether, filtered, washed with ether and petrol. The solid was recrystallised from ether to give the title compound as white crystals, 280 mg (22%), mp 145-6° C.

Workup

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

Sources & evidence

ORD record
ord-75df91fc0a3446fca45bd3017e8ebd5d
Source dataset
uspto-grants-2000_06
Patent number
US06071899

Reaction notes

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