Potassium Carbonate → HCID 21772358, compound

HRID 1277703Notes

Reaction equation

HRID 1277703 reaction equation
[C:1]([NH:4]/[CH:5]=[CH:6]/[S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:22])[C@@H:12]2[C@@H:15](OS(C)(=O)=O)[CH3:16])[C:9]=1[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=[O:24])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([NH:4]/[CH:5]=[CH:6]/[S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:22])/[C:12]/2=[CH:15]\[CH3:16])[C:9]=1[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=[O:24])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86737857HCID 86737857, compound

Product 1

HCID 21772358HCID 21772358, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

p-Nitrobenzyl (5R,6S)-3-[(E)-2-acetamidoethenylthio]-6-[(S)-1-methylsulphonyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (e2) (100 mg) and powdered anhydrous potassium carbonate (62 mg) were stirred in dimethylformamide (2 ml) at room temperature for 30 minutes. The mixture was concentrated in vacuo, and the product was then partitioned between ethyl acetate (20 ml) and water (20 ml). The organic layer was washed with water (2×20 ml) and brine (20 ml), then dried (MgSO4) and evaporated in vacuo. The residue was rapidly chromatographed on silica gel using ethyl acetate as eluant to afford p-nitrobenzyl (5R,6Z)-3-[(E)-2-acetamidoethenylthio]-6-ethylidene-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (e3) (39 mg) as a foam; νmax (CH2Cl2) 1770, 1705 and 1625 cm-1 ; δ(CDCl3) 2.05 (6H, br, s+ d, CH3CO and CH3CH), 3.04 (2H, m, centre of AA'X, 4-CH2) 4.61 (1H, br t, J 8.5 Hz, 5-CH), 5.18 and 5.46 (each 1H, d, J 14 Hz, CH2Ar), 5.82 (1H, d, J 13.5 Hz, =CH.S), 5.90 (1H, m, CH3CH), 7.15 (1H, dd, J 10.5 and 13.5 Hz, NHCH=), 7.58 and 8.13 (each 2H, d, J, 9 Hz, ArCH2), and about 8.05 (1H, br d, NH).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe product was then partitioned between ethyl acetate (20 ml) and water (20 ml)
  3. washThe organic layer was washed with water (2×20 ml) and brine (20 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customThe residue was rapidly chromatographed on silica gel

Sources & evidence

ORD record
ord-1ddc7491772d489f9f41a6fe5a622bc3
Source dataset
uspto-grants-1981_07
Patent number
US04278686

Reaction notes

Loading…