HCID 23470073, compound → HCID 23470056, compound

HRID 867231Notes

Reaction equation

HRID 867231 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[C:12](=[O:13])[NH:11][CH:10]1[CH2:14][S:15]CC1C=CC(OC)=CC=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.C(Cl)Cl.CCOCC>[C:1]([O:5][C:6]([NH:8][CH:9]1[C:12](=[O:13])[NH:11][CH:10]1[CH2:14][SH:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 23470073HCID 23470073, compound

Product 1

HCID 23470056HCID 23470056, compoundYield 55.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 335 mg (0.95 mmole) of 3-t-butoxycarbonylamino-4-oxo-2-(p-methoxybenzylthiomethyl)-azetidine in 5 ml of methanol and 20 ml of methylene chloride is added 1.7 g (5.3 mmole) of mercuric acetate. The mixture is stirred 24 hours under argon, diluted with excess ether and the precipitated mercury adduct filtered and wshed well with ether. The mercury complex is suspended in water, layered with ethyl acetate and hydrogen sulfide gas is passed through the mixture for 1 hour. The mercuric sulfide is removed by filtration, the ethyl acetate layer is separated and washed with brine, dried over magnesium sulfate and evaorated to dryness. Trituration of the residue with 1:1 ethyl acetate-hexane gives 122 mg (55%) of the crystalline title product.

Workup

  1. filtrationthe precipitated mercury adduct filtered
  2. waitis passed through the mixture for 1 hour
  3. customThe mercuric sulfide is removed by filtration
  4. customthe ethyl acetate layer is separated
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-7b317c07771a4fc38b6e9d2bbd2dd4c9
Source dataset
uspto-grants-1978_07
Patent number
US04103086

Reaction notes

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