Réaction #51452

Équation de réaction

4-(4-(furan-3-yl)phenoxy)benzenesulfonyl-tetrahydro-2H-1,4-thiazine-3-carboxylic acid

O-(tert-butyldiphenylsilyl)hydroxylamine

EDC

→

4-(4-(furan-3-yl)phenoxy)benzenesulfonyl-tetrahydro-2H-1,4-thiazine-3-carboxamide

Rendement 14.5%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Autrethe mixture was partitioned between 1 N aq. sodium bisulfate and dichloromethane
2. 2
   ExtractionThe aqueous layer was extracted twice with dichloromethane
3. 3
   Lavagethe combined organic layers were washed with brine
4. 4
   Séchagedried over sodium sulfate
5. 5
   Concentrationconcentrated
6. 6
   AutreThe residue was purified by chromatography on silica gel
7. 7
   Lavageeluting with a gradient from dichloromethane to 5% methanol in dichloromethane

Mode opératoire

To a solution of 3(S)-4-(4-(4-(furan-3-yl)phenoxy)benzenesulfonyl-tetrahydro-2H-1,4-thiazine-3-carboxylic acid (293 mg, 0.62 mmol) and O-(tert-butyldiphenylsilyl)hydroxylamine (0.22 g, 0.8 mmol) in 5 mL of dichloromethane was added EDC (132 mg, 0.69 mmol). After 18 hours at 25° C., the mixture was partitioned between 1 N aq. sodium bisulfate and dichloromethane. The aqueous layer was extracted twice with dichloromethane, and the combined organic layers were washed with brine, dried over sodium sulfate, and concentrated. The residue was purified by chromatography on silica gel, eluting with a gradient from dichloromethane to 5% methanol in dichloromethane, to provide 3(S)-N-(tert-butyldiphenylsilyl)oxy-4-(4-(4-(furan-3-yl)phenoxy)benzenesulfonyl-tetrahydro-2H-1,4-thiazine-3-carboxamide (40 mg, 8%). FAB+MS Calcd for M+Cs+=859.1308 Obs 859.1274; 1HNMR (d6-DMSO): δ 10.81 (s, 1H), 8.17 (s, 1H), 7.74 (s, 1H), 7.67-7.61 (m, 8H), 7.45-7.30 (m, 6H), 7.10 (d, 2H, J=8.83 Hz), 7.00 (d, 2H, J=8.46 Hz), 6.94 (s, 1H), 4.06 (s, 1H), 3.95-3.89 (bm, 1H), 3.77-3.73 (bm, 1H), 2.87-2.78 (bm, 1H), 1.28 (s, 3H), 0.99 (s, 9H), 0.61 (s, 3H)

Source