Ethyl Acetate → HCID 12849728, compound

Participants

Reaction Conditions

Reaction Steps

The formate ester (e4, 425 mg,0.89 mM) was dissolved in 20% aqueous 1,4-dioxan (80 ml) and cooled to 0° C. 0.1 N Sodium hydroxide solution (10.74 ml, 1.07 mM) was added and stirring continued for 5 minutes. Ethylacetate (150 ml) was then added and the organic solution washed with water, saturated sodium chloride solution and dried over anhydrous magnesium sulphate. After filtration, the solvent was removed to yield a pale yellow solid. This solid was chromatographed over silica gel (15 gm). Elution with 10% ethanol/chloroform gave the pure p-nitrobenzyl (5R,6S)-3-(E-2-acetamidoethenylthio)-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo [3.2.0]hept-2-ene-2-carboxylate (e5) as a white solid. This solid was digested in dry diethyl ether and collected by filtration (100 mg), λmax (EtOH) 325 nm (εm 16880), 263 nm (εm 17968), νmax (KBr) 3420, 3260, 1778, 1700, 1675, 1624, 1554, 1520, 1380, 1350, 1335 cm-1 ; δH (d7 -DMF) 10.50 (1H, d. J 10 Hz, NH), 8.30 (2H, d, aromatic protons), 7.85 (2H, d, aromatic protons), 7.22 (1H, dd, J 10 Hz and 14 Hz, NHCH=CH), 6.02 (1H, d, J 14 Hz), 5.47 (2H, q, CH2Ar), 4.28 (dt, 1H, J 3 Hz and 9 Hz, 5-CH), 4.08 (1H, dq, 8-CH), 3.43 (1H, dd, J 3 Hz and 6.3 Hz, 6-CH), 3.27 (2H, ABX, 4-CH2) 2.03 (3H, s, COCH3), 1.23 (3H, d, J 6 Hz, CH3CH).

Provenance & Evidence