As a common heterocyclic compound, it belongs to thiazines compound, name is (S)-4-Hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide, and cas is 154127-42-1, its synthesis route is as follows.
Compound (VII) (112g, 0.313 mol) was suspended in tetrahydrofuran (10 vol). Methanesulfonic anhydride (65.7g, 0.374 moles) was added in one lot and stirred. The reaction mixture was cooled to 0-50C and pyridine (2.5 vol) was added slowly over a period of 45 minutes. The reaction was monitored by TLC [Mobile phase dichloromethane: methanol, 9.5:0.5] for completion. As reaction product the intermediate compound (Vila) was obtained.To the above reaction mixture 70% aqueous ethylamine solution (400 ml, 10 vol) was added slowly at 0-5C. After the complete addition, the reaction mixture was stirred at 25-300C for 12.0 h. The reaction is monitored by TLC [Mobile phase dichloromethane: methanol, 9.5:0.5] for completion. The organic layer (ethylamine and tetrahydrofuran mixture) was distilled off completely below 500C under reduced pressure. The aqueous phase was acidified with concentrated hydrochloric acid and the pH adjusted to 3.0 at 15-25C. The aqueous phase was extracted with t-butyl methyl ether twice (2 x 2.0 vol) to remove any organic impurities if present. The t-butyl methyl ether layer was extracted with 1 N HCI solution and the layers separated.The aqueous layers were combined, treated with activated charcoal and heated at 65-700C. The contents were stirred at 65-700C for 30 minutes, filtered through hyflo supercel at 65-700C and washed with preheated water(65-700C). The filtrate was cooled to 25-30C and the pH was adjusted to 8 with solid sodium bicarbonate. The reaction mixture was stirred for 12 h for crystallization. If the crystallization did not occur, the reaction mass was filtered through a Bchner funnel, extracted with ethyl acetate (3 x 5.0 vol), dried over sodium sulphate and filtered. The organic layer was distilled completely (below 500C) under reduced pressure. The crude product was obtained as a pale yellow syrup, which was washed with hexane (4 x 1.0 vol) to yield a residue which crystallized to a solid on standing.Yield of crude compound (VIIl): 8Og (66.3%)
154127-42-1, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,154127-42-1 ,(S)-4-Hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide, other downstream synthetic routes, hurry up and to see
Reference£º
Patent; AZAD PHARMACEUTICAL INGREDIENTS AG; RAMAKRISHNAN, Arul; SONI, Anil Kumar; ADHIKARI, Sujit Das; RAO, Kommula Srinivasa; PAUL, Soumendu; SRINIVASULU, Ganta; WO2010/103115; (2010); A1;,
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