Application of 154127-42-1, The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.154127-42-1, Name is (S)-4-Hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide, molecular formula is C10H16N2O6S3. In a Article£¬once mentioned of 154127-42-1
Enantioselective synthesis of brinzolamide (AL-4862), a new topical carbonic anhydrase inhibitor. The “DCAT Route” to thiophenesulfonamides
A large scale synthesis of the topical carbonic anhydrase inhibitors AL-4623A (13a-HCl) and AL-4862 (13b) from 3-acetyl-2,5-dichlorothiophene (“DCAT”, 1) is described. Reaction of 1 with NaSBn gave thioether 2, which was converted via sulfenyl chloride 3 and sulfenamide 5 to sulfonamide 6. Bromination of 6 gave bromo ketone 7, which upon reduction with (+)-B-chlorodiisopinocampheylborane and cyclization of the resulting bromohydrin produced S thieno[3,2-e]-1,2-thiazine 8a (96% ee) after chromatography. Treatment of 8a in THF with -BuLi at -70 C resulted in Li-Cl exchange. Reaction of the thienyllithium with SO2 and hydroxylamine O-sulfonic acid afforded bis-sulfonamide 11a. Protection of lia as the acetimidate 12a, followed by tosylation and animation, gave R amine 13a. The synthesis of 13b proceeded via primary sulfonamide 16, which was brominated, reduced, and cyclized to give S thieno[3,2-e]-1,2-thiazine 18 (>98% ee). By virtue of the ionizable NH, 18 was separable from reduction byproducts by base extraction. Alkylation of 18 with 3-bromopropyl methyl ether afforded 8b, which was converted as above, via lib, to AL-4862 (13b). These procedures provided multihundred gram lots of 13a and 13b.
Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. Application of 154127-42-1, If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 154127-42-1, in my other articles.
Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem