Ethanethiol → HCID 20526315, compound

HRID 1577867Notes

Reaction equation

HRID 1577867 reaction equation
[O:1]=[C:2]1[N:8]2[CH:4]([CH2:5][CH:6]=[C:7]2[C:9]([O:11][CH3:12])=[O:10])[CH2:3]1.[CH2:13]([SH:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:13]([S:15][CH:6]1[CH2:5][CH:4]2[N:8]([C:2](=[O:1])[CH2:3]2)[CH:7]1[C:9]([O:11][CH3:12])=[O:10])[CH3:14]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 12796955HCID 12796955, compound

Product 1

HCID 20526315HCID 20526315, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of methyl 7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate (9) (0.050 g) in dry dimethylformamide (1 ml) at room temperature was treated with ethane thiol (0.10 ml) followed by powdered potassium carbonate (0.023 g). After a period of 1 hour, the excess thiol was blown off in a stream of argon and the residue concentrated at 30° under reduced pressure. The residual gum was dissolved in ethyl acetate, washed with brine and dried over sodium sulphate. The ethyl acetate solution was concentrated and the three diastereoisomers (10, 11 and 12 in order of increasing polarity) were separated by column chromatography on silica gel 60 (<230 mesh), eluting with 60°-80° petroleum ether/ethyl acetate 7:3.

Workup

  1. concentrationthe residue concentrated at 30° under reduced pressure
  2. dissolutionThe residual gum was dissolved in ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationThe ethyl acetate solution was concentrated
  6. temperaturethe three diastereoisomers (10, 11 and 12 in order of increasing polarity)
  7. customwere separated by column chromatography on silica gel 60 (<230 mesh)
  8. washeluting with 60°-80° petroleum ether/ethyl acetate 7:3

Sources & evidence

ORD record
ord-10369748f49d4bd4af193e24b4091a05
Source dataset
uspto-grants-1981_09
Patent number
US04289696

Reaction notes

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