Propylene Oxide → HCID 53640453, compound

HRID 436035Notes

Reaction equation

HRID 436035 reaction equation
[CH3:1][O:2][C:3]([CH:5]([N:9]1[CH:12]([S:13][N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])[CH:11]([NH:25][C:26](=[O:35])[CH2:27][O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:10]1=[O:36])[C:6]([CH3:8])=[CH2:7])=[O:4].C1OC1C.[Br:41]N1C(=O)CCC1=O>ClCCCl.[Hg]>[CH3:1][O:2][C:3]([CH:5]([N:9]1[CH:12]([S:13][N:14]2[C:15](=[O:24])[C:16]3=[CH:23][CH:22]=[CH:21][CH:20]=[C:17]3[C:18]2=[O:19])[CH:11]([NH:25][C:26](=[O:35])[CH2:27][O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:10]1=[O:36])[C:6]([CH2:8][Br:41])=[CH2:7])=[O:4]

Participants

6

Reactant 3

HCID 6378Propylene OxideHCID 67184N-bromobutanimideHCID 54321043HCID 54321043, compound

Product 1

HCID 53640453HCID 53640453, compoundYield 34.3%

Reagents, catalysts & solvents 2

HCID 23931MercuryCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 1-(1-methoxycarbonyl-2-methylprop-2-enyl)-3-phenoxyacetamido-4-phthalimidothio-azetidin-2-one 3.6 g (7 mmoles) in 230 ml of 1,2-dichloroethane were added 5 ml of propylene oxide and 1.9 g (10.5 mmoles) of N-bromosuccinimide. The mixture was irradiated under nitrogen for 2 hours at 14° C with a Hanovia TQ 150 mercury high pressure lamp using a Pyrex filter. After washing twice with 150 ml of a 0.067 molar aqueous potassium phosphate solution buffered to pH 5.8, washing twice with 100 ml of water, drying and treating with decolorizing charcoal, the reaction mixture was concentrated. After adding a mixture of ethyl acetate, diethyl ether and n - hexane, the precipitate was chromatographed on silica gel (methylene chloride ethyl acetate 9:1 (v/v) to obtain 1.3 g (2.4 mmoles; 34% yield) of 1-(1-methoxycarbonyl-2-bromomethylprop-2-enyl)-3-phenoxyacetamido-4-phthalimidothio-azetidin-2-one.

Workup

  1. filtrationfilter
  2. washAfter washing twice with 150 ml of a 0.067 molar aqueous potassium phosphate solution
  3. washwashing twice with 100 ml of water
  4. customdrying
  5. additiontreating with decolorizing charcoal
  6. concentrationthe reaction mixture was concentrated
  7. additionAfter adding
  8. additiona mixture of ethyl acetate, diethyl ether and n - hexane
  9. customthe precipitate was chromatographed on silica gel (methylene chloride ethyl acetate 9:1 (v/v)

Sources & evidence

ORD record
ord-7ab621e6e3d945e6b86ef0eff9c6bce0
Source dataset
uspto-grants-1977_02
Patent number
US04007202

Reaction notes

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