Potassium Acetate → HCID 21772272, compound

HRID 1277708Notes

Reaction equation

HRID 1277708 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:24])[C@H:12]2[C@@H:15](OS(OCC)(=O)=O)[CH3:16])[C:9]=1[C:25]([O:27][CH3:28])=[O:26])(=[O:3])[CH3:2].C([O-])(=O)C.[K+]>C(O)C>[C:1]([NH:4]/[CH:5]=[CH:6]/[S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:24])/[C:12]/2=[CH:15]/[CH3:16])[C:9]=1[C:25]([O:27][CH3:28])=[O:26])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 517044Potassium AcetateHCID 21772260HCID 21772260, compound

Product 1

HCID 21772272HCID 21772272, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl (5R,6R)-3-[(E)-2-acetamidoethenylthio]-6-[(S)-1-ethoxysulphonyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (e22) (42 mg) was taken up in ethanol (2 ml) and treated with anhydrous potassium acetate (50 mg). After 90 minutes the solvent was removed by evaporation and the product dissolved in ethyl acetate (10 ml) and washed with water (10 ml), and with brine (10 ml) and then dried (MgSO4) and evaporated. The i.r. and u.v. spectra of crude material showed that the ethylidene compound had been formed. This was purified by chromatography on silica gel to give methyl (5R,6E)-3-[(E)-2-acetamidoethenylthio]-6-ethylidene-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (e34) (14 mg). νmax (CH2Cl2) 1780, 1705, 1625 cm-1. δ[CDCl3 +1 drop (CD3)2CO] 1.79 (3 H, d, J 7 Hz, CH3CH=), 2.02 (3H, s, CH3CO), 2.90 (1H, dd, J 18 Hz and 8.5 Hz, HA of ABX), 3.16 (1H, dd, J 18 and 9.5 Hz, HB of ABX), 3.78 (3H, s, OCH3), 4.69 (1H, broad t, CH.CH2), 5.84 (1H, d, J 14 Hz SCH:CH), 6.33 (1H, broad q, J 7 Hz, CH3CH=), 7.18 (1H, dd, J 14 and 10 Hz, NH.CH=CH), 8.86 (1H, broad d, J 10 Hz, CONH.CH) p.p.m.

Workup

  1. customAfter 90 minutes the solvent was removed by evaporation
  2. dissolutionthe product dissolved in ethyl acetate (10 ml)
  3. washwashed with water (10 ml)
  4. dry with materialwith brine (10 ml) and then dried (MgSO4)
  5. customevaporated
  6. customhad been formed
  7. customThis was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-50c4f801fd194ff69db4d10d102d0470
Source dataset
uspto-grants-1981_07
Patent number
US04278686

Reaction notes

Loading…