HCID 11101284, compound → 3-t-Butoxycarbonylamino-3-methyl-N-[3,4-dihydro-1,4-dioxo-1,5-benzothiazepin-3(S)-yl]-butanamide

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Reaction Steps

A solution of 179 mg (0.46 mmol) of 3-t-butoxycarbonylamino-3-methyl-N-[3,4-dihydro-4-oxo-1,5-benzothiazepin-3(S)-yl]-butanamide (Example 46, Step A) in 4.5 mL of methanol/water (5:1) was treated with 102 mg (0.48 mmol, 1.05 eq) of sodium periodate and stirred at room temperature for 48 hours. The reaction mixture was filtered and the filtrate concentrated under vacuum. The residue was redissolved in chloroform, dried over potassium carbonate, filtered and concentrated under vacuum. Purification by flash chromatography on silica, eluting with ethyl acetate, afforded 47 mg (0.12 mmol, 25%) of the less polar, minor diastereomer A in addition to 105 mg (0.26 mmol, 56%) of the more polar, major diastereomer B. 1H NMR (diastereomer A; 200 MHz, CDCl3): 1.37 (s,3H), 1.38 (s,3H), 1.45 (s,9H), 2.51 (d,13 Hz,1H), 2.79 (d,13 Hz,1H), 3.80 (m,2H), 4.78 (m,1H), 4.95 (br s,1H), 7.14 (m,2H), 7.59 (m,2H), 7.93 (m,1H), 8.18 (br s,1H). FAB-MS: calculated for C19H27N3O5S 409; found 410 (M+H,29%).

Provenance & Evidence