Acetone → HCID 9543435, compound

Participants

Reaction Steps

A suspension of α-hydroxybenzyl polystyrene - 2% divinylbenzene coplymer [(10.0g., 0.029 mole) prepared according to the method G. L. Southard et al; Tetrahedron 1971, 27, 2701] in methylene chloride (50 ml.) was stirred for 1 hour at room temperature (18°-21°) to swell the polymer. To the suspension cooled to 5° was added (1S, 3S, 5R,6R)-2,2-dimethyl-6-phenylacetamidopenam-3-carboxylic acid 1-oxide acetone solvate (20.40 g., 0.05 mole), followed by Toluene-p-sulphonyl chloride (14.30g., 0.075 mole), pyridine (12.1 ml., 11.85g., 0.15 mole; dried over KOH) and acetone (25 ml.). The mixture was stirred for 4 hours at 5°- 10°, during which an intense green colouration developed. The reaction mixture was filtered and pulled as dry as possible. The product was washed with chloroform (3 × 100 ml., containing 2% v/v ethanol), methanol (2 × 100 ml.), water (4 × 100 ml.), methanol (2 × 10 ml.) and chloroform (2 × 100 ml., containing 2% v/v ethanol); and drid to constant weight in vacuo at room temperature (18°-21°) to give a pale yellow polymer ester of (1S, 3S, 5R, 6R)-2,2-dimethyl-6-phenylacetamidopenam-3-carboxylic acid 1-oxide (19.97g.). The composition was confirmed by microanalytical data and the infra red spectrum was identical with the product obtained in example 6 above. From the gain in weight, the penicillin moiety corresponds to 1.43 m.mole/g. of polymer.

Provenance & Evidence