Thiophenol → HCID 21246127, compound

HRID 1252773Notes

Reaction equation

HRID 1252773 reaction equation
[N:1]12[C:7](=[O:8])[CH2:6][CH:5]1[CH2:4][C:3](=O)[CH:2]2[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].C(N(CC)C(C)C)(C)C.P(Cl)(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.[C:46]1([SH:52])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>C(#N)C.C(OCC)(=O)C.C1C=CC=CC=1>[C:46]1([S:52][C:3]2[CH2:4][CH:5]3[N:1]([C:7](=[O:8])[CH2:6]3)[C:2]=2[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

8

Reactant 4

HCID 7969ThiophenolHCID 75654Diphenyl chlorophosphateHCID 81531Diisopropylethylamine2×HCID 12804725Benzyl 3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate

Product 1

HCID 21246127HCID 21246127, compoundYield 96.8%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

An ice-cold solution of benzyl 1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate (13 mg, 0.05 mmol) in anhydrous acetonitrile is treated with N,N-diisopropylethylamine (10.4 μl, 0.06 mmol) and diphenyl chlorophosphate (10.9 μl, 0.053 mmol) and the resulting solution is stirred in the cold and under a nitrogen atmosphere for 90 mins. More N,N-diisopropylethylamine (8.7 μl, 0.05 mmol) and thiophenol (5.1 μl, 0.05 mmol) are added and the reaction mixture is stirred in the cold for 2 hours. The resulting mixture is combined with a second similar run, diluted with ethyl acetate to 10 ml volume, washed with water, 1M pH3 phosphate buffer, 5% aqueous sodium bicarbonate, and brine, dried over magnesium sulfate, and evaporated under vacuum to an oil (34 mg). This material is purified on a 0.25 mm×20×20 silica gel GF plate using 3:1 toluene-ethyl acetate as developing solvent. The UV visible band at Rf 0.55 is removed and eluted with ethyl acetate. Evaporation of the solvent leaves a residue which is lyophilized from benzene to provide benzyl 3-phenylthio-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (17 mg) as an amorphous, white powder.

Workup

  1. stirringthe reaction mixture is stirred in the cold for 2 hours
  2. washwashed with water, 1M pH3 phosphate buffer, 5% aqueous sodium bicarbonate, and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under vacuum to an oil (34 mg)
  5. customThis material is purified on a 0.25 mm×20×20 silica gel GF plate
  6. customThe UV visible band at Rf 0.55 is removed
  7. washeluted with ethyl acetate
  8. customEvaporation of the solvent
  9. customleaves a residue which

Sources & evidence

ORD record
ord-88cca693125e406cbe3ac045e0a57203
Source dataset
uspto-grants-1988_05
Patent number
US04745188

Reaction notes

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