5708-19-0

Basic information

• Product Name: (S)-(-)-3-CYCLOHEXENECARBOXYLIC ACID
• Synonyms: (S)-(-)-3-CYCLOHEXENECARBOXYLIC ACID;(1S)-cyclohex-3-ene-1-carboxylic acid;(S)-Cyclohex-3-enecarboxylic acid;(S)-3-Cyclohexene-1-carboxylic Acid;(S)-(?)-1,2,3,6-Tetrahydrobenzoic acid;(1S)-3-Cyclohexene-1-carboxylic acid;(S)-(-)-3-Cyclohexene-1-carboxylic Acid
• CAS NO: 5708-19-0
• Molecular Formula: C₇H₁₀O₂
• Molecular Weight: 126.15
• EINECS: 1592732-453-0
• Product Categories: Edoxaban
• Mol File: 5708-19-0.mol
• Article Data: 28

Chemical Properties

• Melting Point: 19°C(lit.)
• Boiling Point: 118°C/6mmHg(lit.)
• Flash Point: 109.903 °C
• Appearance: /
• Density: 1.126 g/cm³
• Refractive Index: 1.4780 to 1.4820
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 4.67±0.20(Predicted)
• CAS DataBase Reference: (S)-(-)-3-CYCLOHEXENECARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-3-CYCLOHEXENECARBOXYLIC ACID(5708-19-0)
• EPA Substance Registry System: (S)-(-)-3-CYCLOHEXENECARBOXYLIC ACID(5708-19-0)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8 / PGIII
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 5708-19-0(Hazardous Substances Data)

Usage

Description

(S)-(-)-3-Cyclohexenecarboxylic acid is an organic compound with the molecular formula C7H10O2. It is a chiral molecule, which means it has a non-superimposable mirror image, and in this case, it is the (S)-enantiomer. (S)-(-)-3-Cyclohexenecarboxylic acid is characterized by a cyclohexene ring with a carboxylic acid functional group attached to the third carbon. It is a versatile building block in organic synthesis and has potential applications in the pharmaceutical industry.

Uses

(S)-(-)-3-Cyclohexenecarboxylic acid is used as an organic synthesis intermediate for the preparation of various chemical compounds. It is particularly useful in the development of pharmaceuticals, where it can be employed to create novel drug candidates with potential therapeutic applications.
Used in Pharmaceutical Industry:
(S)-(-)-3-Cyclohexenecarboxylic acid is used as a pharmaceutical intermediate for the synthesis of N-[(1R,2S,5S)-2-[(5-chloroindol-2-yl)carbonyl]amino-5-(dimethylcarbamoyl)cyclohexyl]-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxamide hydrochloride. (S)-(-)-3-Cyclohexenecarboxylic acid is a potent and orally active direct inhibitor of factor Xa, which plays a crucial role in the coagulation cascade. Inhibiting factor Xa can help in the treatment of various thrombotic disorders, such as deep vein thrombosis and pulmonary embolism.
Additionally, (S)-(-)-3-Cyclohexenecarboxylic acid can be used in laboratory research and development processes, where it may contribute to the discovery of new chemical entities with potential applications in various fields, including but not limited to, pharmaceuticals, agrochemicals, and materials science.

Synthesis

54.94 g of cyclohex-3-ene-1(S)-carboxylic acid (R)-(+)-methylbenzylamine salt and 18.2 volumes of H2O were charged to a flask at 20-25°C and stirred. To the mixture obtained further 6.7 volumes of H2O and 10 volumes of EtOAc were added. The mixture obtained was stirred for 15 min, the phases were separated and the organic layer was discarded. The aqueous layer was treated with 10 volumes of MTBE and 2.5 equivalents of 6M HCI were added slowly. The mixture obtained was stirred and two layers were formed, separated and the aqueous layer was extracted with MTBE. The organic layers obtained were combined and washed with aqueous, 30percent NaCl solution. The organic phase obtained was dried over Na2S04, filtered, and from the filtrate obtained solvent was removed in vacuo. Cyclohex-3-ene-1(S)-carboxylic acid in the form of a clear oil was obtained. Yield: 26.13 g (93.3percent of theory).

Upstream product

• 72581-32-9 cyclohex-3-enylmethanol 
• 5709-99-9 (R)-1-C-(1-Cyclohexen-5-yl)methanol 
• 5681-56-1 (S)-4-(Hydroxymethyl)cyclohexene 
• 131556-48-4 (S)-Cyclohex-3-enyl-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-methanone 
• 102096-64-0 3-Cyclohexene-1-carboxylic acid (R)-pentalactone ester 
• 102096-64-0 (S)-Cyclohex-3-enecarboxylic acid 4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester 
• 102096-60-6 (R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl acrylate 
• 106-99-0 buta-1,3-diene 
• 6493-77-2 methyl cyclohex-3-ene-1-carboxylate 
• 15111-56-5 ethyl-3-cyclohexene-1-carboxylate 
• 1228540-49-5 Ethyl (R)-3-cyclohexene-1-carboxylate 
• 4771-80-6 1,2,5,6-tetrahydrobenzoic acid 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 6493-77-2 (R)-(+)-methyl 3-cyclohexene-1-carboxylate 

Downstream Products

• 123536-66-3 (1S,4S,5S)-4-iodo-6-oxabicyclo<3.2.1>octan-7-one 
• 163812-76-8 (1S,2S,4S)-4-(hydroxymethyl)-1-iodo-2-cyclohexanol 
• 123536-65-2 (5S)-5-hydroxymethyl-2-cyclohexen-1-one 
• 6493-77-2 (S)-(-)-methyl 3-cyclohexene-1-carboxylate 
• 1350734-43-8 {(1S,2S,4S)-4-[(tert-butoxycarbonyl)-amino]-2-hydroxy-cyclohexyl}-benzene-carbothioate 
• 1350734-44-9 {(1R,2R,5S)-5-[(tert-butoxycarbonyl)amino]-2-hydroxycyclohexyl}benzene-carbothioate 
• 1352833-87-4 tert-Butyl [(1S,3S,4S)-3-hydroxy-4-mercapto-cyclohexyl]-carbamate 
• 480452-36-6 carbamic acid, N-[(1R,2S,5S)-2-[[2-[(5-chloro-2-pyridinyl)amino]-2-oxoacetyl]amino]-5-[(dimethylamino)carbonyl]cyclohexyl]-1,1-dimethylethyl ester 
• 480449-70-5 edoxaban 
• 929693-31-2 {(1R,2R,4S)-2-[(tert-butoxycarbonyl)amino]-4-[(dimethylamino)carbonyl]cyclohexyl}methanesulfonate 

Relevant articles and documents

Kinetic Resolution of Nearly Symmetric 3-Cyclohexene-1-carboxylate Esters Using a Bacterial Carboxylesterase Identified by Genome Mining

A new bacterial carboxylesterase (CarEst3) was identified by genome mining and found to efficiently hydrolyze racemic methyl 3-cyclohexene-1-carboxylate (rac-CHCM) with a nearly symmetric structure for the synthesis of (S)-CHCM. CarEst3 displayed a high substrate tolerance and a stable catalytic performance. The enantioselective hydrolysis of 4.0 M (560 g·L-1) rac-CHCM was accomplished, yielding (S)-CHCM with a >99% ee, a substrate to catalyst ratio of 1400 g·g-1, and a space-time yield of 538 g·L-1·d-1.

Preparation method of edoxaban tosylate and isomers thereof

The invention discloses a preparation method of edoxaban tosylate and isomers thereof. By taking a compound (I) and a compound (II) as starting materials, the method can be used to prepare any one ofhigh-purity edoxaban tosylate (1S, 2R, 4S), edoxaban tosylate enantiomers (1R, 2S, 4R), edoxaban tosylate epimers (1R, 2R, 4S) and edoxaban tosylate epimers (1S, 2S, 4R). Effective guarantee is provided for process research and quality control of the edoxaban tosylate bulk drug and related preparations, the preparation method is suitable for commercialization, the produced edoxaban tosylate bulk drug is high in purity and has great significance and practical value, and the production of the edoxaban tosylate bulk drug and the control of drug quality are facilitated.

Preparation method of edoxaban

The invention relates to a new preparation route and a new method for a p-toluenesulfonic acid edoxaban hydrate and intermediates thereof. The new method comprises the steps that a high-reactivity compound 109A4x is prepared; a compound 109C6x is prepared by using a new synthesizing method; new compounds 109E8-01, 109E9x and 109T7-01 are prepared; the p-toluenesulfonic acid edoxaban hydrate is prepared by using the intermediates. By using the new method and the new route, the reaction step of copious cooling is omitted, and dangerous elemental sulfur, high-risk n-butyllithium and high-risk azides are prevented from being used. In a word, by means of the method, the p-toluenesulfonic acid edoxaban hydrate and the key intermediates thereof are more easily and safely prepared at a lower coston an industrialization scale.