Sulfuric Acid → HCID 18442428, compound

Participants

Reaction Conditions

Reaction Steps

To LiAlH4 (5.76 g, 151 mmol) were added THF (200 ml). The reaction mixture was cooled to 0° C. and H2SO4 (4.06 ml, 76 mmol) were added slowly with a syringe. After the addition was completed the reaction was stirred for 10 minutes, Then 1,1-dioxo-3,3-dibutyl-4-oxo-5-(4-nitrophenyl)-8-methoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 104; 2.57 g, 5.06 mmol) dissolved in THF (50 ml) was added at 0° C. After vigorous stirring for 1 hour the cooling bath was removed and the reaction was heated to 40° C. overnight. Then Na2SO4.10H2O (3–4 teaspoons), water (8 ml), NaOH (15%, aq) (8 ml), water (25 ml) and MeOH (30 ml) were added in that order. The precipitate was removed by filtration and rinsed with DCM/MeOH. The solvent was dried, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography using DCM:EtOAc, 9:1 then 3:1 as eluent to give the title compound 0.6 g (27%). M/z 431.3.

Provenance & Evidence