HCID 21896694, compound → HCID 21896664, compound

Participants

Reaction Steps

1,1-Dioxo-2-(4-methoxybenzyl)-3,3-dibutyl-5-phenyl-7-methylthio-8-(t-butoxycarbonylmethoxy)-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepine (Method 25; 6.902 g, 10.11 mmol) was dissolved in a mixture of TFA (50 ml) and Et3Si (8 ml) and the solution was stirred for 90 min at RT. The solvent was removed under reduced pressure and the residue was dissolved in t-BuOMe (100 ml). The organic phase was washed with water (20 ml) and then extracted three times with diluted NaOH (2×50 ml 0.5M). The combined aqueous extracts were acidified with diluted HCl (70 ml, 1M) (pH 1–2) and were then extracted twice with t-BuOMe (2×50 ml). The ether layer was washed with brine, dried over MgSO4 and concentrated. 4.694 g (92%) of the desire product as brown oil were obtained. NMR (400 MHz, CD3OD): 0.70–0.85 (m, 6H), 1.00–1.25 (m, 6H), 1.25–1.50 (m, 4H), 1.55–1.70 (m 2H), 2.10 (s, 3H), 3.90 (brs, 2H), 4.55 (s, 2H), 6.60 (s, 1H), 6.95–7.35 (m, 6H).

Provenance & Evidence