p-Toluenesulfonic acid → HCID 131721510, compound

Participants

Reaction Steps

4-Methoxybenzyl (RS)-2-hydroxy-2-[(lR,5R)-3-benzyl-4-thia-2,6-diazabicyclo[3.2.0)hept-2-en-7-on-6-yl]acetate (6.0 g, 14.6 mmol) in 50% acetone/dichloromethane (60 ml) was cleaved with 4-toluenesulphonic acid (5.0 g, 26.3 mmol) in water (12 ml). The product was reacted with crude bromide from Example 34 (e) (3.40 g, 13.4 mmol) in acetone (70 ml) followed by potassium carbonate (1.0 g, 7.2 mmol) as described in Example 6 (b). After work-up, the residue was purified by chromatography on silica gel eluting with 50, 70 and 100% ethyl acetate in hexane to yield the title compound (3.40 g, 42%); νmax (CH2Cl2) 3400, 1781, 1735, 1682, 1613 and 1516 cm-1. (Mass spectrum: +ve ion (3-nitrobenzyl alcohol, sodium acetate) MNa+ (625)].

Provenance & Evidence