Sodium Sulfite → HCID 19605313, compound

HRID 1603641Notes

Reaction equation

HRID 1603641 reaction equation
[CH2:1]([S:8][CH:9]1[N:12]([CH2:13][C:14](=[O:23])[CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11](=[O:24])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:33])C=1.S([O-])([O-])=O.[Na+].[Na+].C(=O)([O-])O.[Na+]>ClCCl>[CH2:1]([S:8]([CH:9]1[N:12]([CH2:13][C:14](=[O:23])[CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11](=[O:24])[CH2:10]1)=[O:33])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 9884329HCID 9884329, compound

Product 1

HCID 19605313HCID 19605313, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-(benzylthio)-1-(4-phenyl-2-oxobutyl)azetidin-2-one (3.1 g, 9.2 mmol) in dichloromethane (100 ml) was cooled to -50 to -60° C. and a solution of m-chloroperbenzoic acid (1.9 g, 11 mmol) in dichloromethane (80 ml) added dropwise with stirring over 30 min. After a further 30 min at -50 to -60° C. the reaction mixture was shaken with a mixture of saturated aqueous sodium sulphite and saturated sodium hydrogen carbonate and the organic layer separated, dried (MgSO4) and evaporated to a solid. Two recrystallisations from ethyl acetate gave (4R,SR/4S,SS) 4-(benzylsulphinyl)-1-(4-phenyl-2-oxobutyl)azetidin-2-one (0.8 g, 27%), mp 147-9° C.

Workup

  1. customthe organic layer separated
  2. dry with materialdried (MgSO4)
  3. customevaporated to a solid
  4. customTwo recrystallisations from ethyl acetate

Sources & evidence

ORD record
ord-8042ac6d203a4b4989dd43a36618c7db
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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