反应详情

A mixture of p-toluenesulfonic acid monohydrate (788 mg., 4.14 mmoles), acetone (35 ml.) and 6-triphenylmethylamino-2,2-dimethyl-3-(5-tetrazolyl)penam (2.0 g., 4.14 mmole) is stirred for twenty minutes at room temperature and is then diluted with water (100 ml.) and isopropylether (100 ml.). The biphasic mixture is stirred vigorously and adjusted to pH 7 with 2 N sodium hydroxide. Phenylacetyl chloride (700 mg., 4.55 mmole freshly distilled) is added and the reaction mixture maintained at pH 5.5-6.5 by addition of 2 N sodium hydroxide as necessary. Reaction is continued until the pH levels off at 6.5. The two phases are separated and the aqueous phase is washed with ether (2×50 ml.). Chloroform (100 ml.) is added and the pH is adjusted to 2 by addition of 6 N HCl. The mixture is stirred, the phases separated and the aqueous phase extracted with chloroform (2×50 ml.). The chloroform phases are combined, dried (Na2SO 4), and then concentrated under reduced pressure to about 50 ml. volume. A 1:1 solution of ether-hexane is added dropwise with vigorous stirring until precipitation of the product is complete. The white precipitate is filtered and air-dried. The yield is 850 mg. (57.4%), m.p. 168°-170°. NMR (DMSO-d6): 7.30 (s, 5H), 5.80-5.42 (m, 2H), 5.28 (s, 1H), 3.60 (s, 2H), 1.68 (s, 3H) and 1.10 ppm (s, 3H).

1. stirringThe biphasic mixture is stirred vigorously
2. distillation, 4.55 mmole freshly distilled)
3. additionis added
4. temperaturethe reaction mixture maintained at pH 5.5-6.5 by addition of 2 N sodium hydroxide as necessary
5. customReaction
6. customThe two phases are separated
7. washthe aqueous phase is washed with ether (2×50 ml.)
8. additionChloroform (100 ml.) is added
9. additionthe pH is adjusted to 2 by addition of 6 N HCl
10. stirringThe mixture is stirred
11. customthe phases separated
12. extractionthe aqueous phase extracted with chloroform (2×50 ml.)
13. dry with materialdried (Na2SO 4)
14. concentrationconcentrated under reduced pressure to about 50 ml
15. additionA 1:1 solution of ether-hexane is added dropwise
16. stirringwith vigorous stirring until precipitation of the product
17. filtrationThe white precipitate is filtered
18. customair-dried