160982-16-1

Basic information

• Product Name: (S)-6-CHLORO-1,1-DIOXO-1,2,3,4-TETRAHYDRO-1LAMBDA*6*-THIENO[3,2-E][1,2]THIAZIN-4-OL
• Synonyms: (4S)-1,1-dioxide-6-chloro-3,4-dihydro-2H-Thieno[3,2-e]-1,2-thiazin-4-ol;(S)-3,4-Dihydro-6-chloro-4-hydroxy-2H-thieno[3,2-e]-1,2-thiazine-1,1-dioxide;(S)-3,4-Dihydro-6-chloro-4-hydroxy-4H-thieno[3,2-e]-1,2-thiazine-1,1-dioxide;(S)-6-Chloro-4-hydroxy-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine 1,1-dioxide;(s)-6-chloro-1,1-dioxo-1,2,3,4-tetrahydro-1laMbad*6*-thieno[3,2-e][1,2] thiazin-4-ol;(S)-6-CHLORO-1,1-DIOXO-1,2,3,4-TETRAHYDRO-1LAMBDA*6*-THIENO[3,2-E][1,;(S)-6-Chloro-4-hydroxy-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine 1,1-Dioxide;2H-Thieno[3,2-E]-1,2-ThiaziN-4-Ol,6-Chloro-3,4-Dihydro-, 1,1-Dioxide, (4S-
• CAS NO: 160982-16-1
• Molecular Formula: C6H6ClNO3S2
• Molecular Weight: 239.7
• EINECS: 1533716-785-6
• Mol File: 160982-16-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 128.0 to 132.0 °C
• Boiling Point: 427.885 °C at 760 mmHg
• Flash Point: 212.578 °C
• Appearance: /
• Density: 1.746 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.664
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: soluble in Methanol
• PKA: 9.72±0.40(Predicted)
• CAS DataBase Reference: (S)-6-CHLORO-1,1-DIOXO-1,2,3,4-TETRAHYDRO-1LAMBDA*6*-THIENO[3,2-E][1,2]THIAZIN-4-OL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-6-CHLORO-1,1-DIOXO-1,2,3,4-TETRAHYDRO-1LAMBDA*6*-THIENO[3,2-E][1,2]THIAZIN-4-OL(160982-16-1)
• EPA Substance Registry System: (S)-6-CHLORO-1,1-DIOXO-1,2,3,4-TETRAHYDRO-1LAMBDA*6*-THIENO[3,2-E][1,2]THIAZIN-4-OL(160982-16-1)

Safety Data

• Hazardous Substances Data: 160982-16-1(Hazardous Substances Data)

Usage

General Description

(S)-6-Chloro-1,1-dioxo-1,2,3,4-tetrahydro-1lambda*6*-thieno[3,2-e][1,2]thiazin-4-ol is a chemical compound with the molecular formula C4H3ClNO3S2. It is a heterocyclic compound that contains both oxygen and sulfur atoms in its ring structure. (S)-6-CHLORO-1,1-DIOXO-1,2,3,4-TETRAHYDRO-1LAMBDA*6*-THIENO[3,2-E][1,2]THIAZIN-4-OL may have potential pharmaceutical applications due to its unique structure, and it could be used in the development of new drugs or as a reagent in chemical reactions. Further research and analysis are necessary to fully understand the properties and potential uses of this chemical compound.

InChI:InChI=1/C6H6ClNO3S2/c7-5-1-3-4(9)2-8-13(10,11)6(3)12-5/h1,4,8-9H,2H2/t4-/m1/s1

Upstream product

• 160982-09-2 3-Acetyl-2-(phenylmethyl)thio-5-chlorothiophene 
• 36157-40-1 3-acetyl-2,5-dichlorothiophene 
• 160982-11-6 3-(2-Bromoacetyl)-5-chloro-thiophene-2-sulfonamide 
• 1634-04-4 tert-butyl methyl ether 
• 124-38-9 carbon dioxide 

Downstream Products

• 138890-62-7 brinzolamide 
• 154127-42-1 (S)-3,4-dihydro-4-hydroxy-2(3-methoxypropyl)-4H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide-1,1-dioxide 
• 160982-13-8 (S)-3,4-dihydro-6-chloro-4-hydroxy-2-(3-methoxypropyl)-4H-thieno[3,2-e]-1,2-thiazine 1,1-dioxide 
• 171273-35-1 2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamine 1,1-dioxide 

Relevant articles and documents

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.