365997-33-7

Basic information

• Product Name: (1S,3R,4R)-3-(Boc-aMino)-4-hydroxy-cyclohexanecarboxylic acid ethyl ester
• Synonyms: Cyclohexanecarboxylic acid,3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-hydroxy-, ethyl ester,(1S,3R,4R)-;Ethyl (1S,3R,4R)-3-(tert-butoxycarbonylamino)-4-hydroxycyclohexane-1-carboxylate;(1S,3R,4R)-(+)-3-[(tert-Butoxycarbonyl)amino]-4-hydroxycyclohexanecarboxylic acid ethyl ester;(1S,3R,4R)-3-(Boc-aMino)-4-hydroxy-cyclohexanecarboxylic acid ethyl ester
• CAS NO: 365997-33-7
• Molecular Formula: C₁₄H₂₅NO₅
• Molecular Weight: 287.352
• Mol File: 365997-33-7.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 406.6±45.0 °C(Predicted)
• Appearance: /
• Density: 1.12±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly), DMSO (Slightly), Ethyl Acetate (Slightly)
• PKA: 11.73±0.60(Predicted)
• CAS DataBase Reference: (1S,3R,4R)-3-(Boc-aMino)-4-hydroxy-cyclohexanecarboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,3R,4R)-3-(Boc-aMino)-4-hydroxy-cyclohexanecarboxylic acid ethyl ester(365997-33-7)
• EPA Substance Registry System: (1S,3R,4R)-3-(Boc-aMino)-4-hydroxy-cyclohexanecarboxylic acid ethyl ester(365997-33-7)

Safety Data

• Hazardous Substances Data: 365997-33-7(Hazardous Substances Data)

Usage

Description

(1S,3R,4R)-3-(Boc-aMino)-4-hydroxy-cyclohexanecarboxylic acid ethyl ester, also known as Ethyl (1S,3R,4R)-3-(tert-butoxycarbonylamino)-4-hydroxycyclohexane-1-carboxylate, is a complex organic compound with a unique molecular structure. It is characterized by its specific stereochemistry, which is crucial for its applications in chemical synthesis. (1S,3R,4R)-3-(Boc-aMino)-4-hydroxy-cyclohexanecarboxylic acid ethyl ester is a versatile building block that can be utilized in the preparation of various pharmaceuticals and other chemical products.

Uses

Used in Pharmaceutical Industry:
(1S,3R,4R)-3-(Boc-aMino)-4-hydroxy-cyclohexanecarboxylic acid ethyl ester is used as a building block for the preparation of six stereoisomers of diaminocyclohexane carboxamide. These stereoisomers serve as key intermediates in the synthesis of factor Xa inhibitors, which are important anticoagulant drugs used to prevent blood clot formation and treat related conditions.
Used in Chemical Synthesis:
In the field of chemical synthesis, (1S,3R,4R)-3-(Boc-aMino)-4-hydroxy-cyclohexanecarboxylic acid ethyl ester is employed as a valuable starting material for the creation of various complex molecules. Its unique structure allows for the development of new compounds with potential applications in different industries, such as pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 365997-32-6 ethyl (1S,3R,4R)-3-azido-4-hydroxycyclohexane-1-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 929693-34-5 ethyl (1S,3R,4R)-3-amino-4-hydroxycyclohexanecarboxylate 
• 123536-66-3 (1S,4S,5S)-4-iodo-6-oxabicyclo<3.2.1>octan-7-one 
• 67976-82-3 (1S)-3-cyclohexene-1-carboxylic acid (R)-(+)-α-methylbenzylamine salt 
• 4771-80-6 1,2,5,6-tetrahydrobenzoic acid 
• 5708-19-0 (1S)-3-cyclohexenecarboxylic acid 
• 139893-81-5 (1S,4S,5S)-4-bromo-6-oxabicyclo<3.2.1>octan-7-one 
• 365997-31-5 (1S,3S,6R)-7-oxabicyclo[4.1.0]heptane-3-carboxylic acid ethyl ester 
• 75281-54-8 ethyl 7-oxabicyclo<4.1.0>heptane-3-carboxylate 
• 636-82-8 cyclohexene-1-carboxylic acid 

Downstream Products

• 365997-36-0 (1S,3R,4R)-3-[(tert-butoxycarbonyl)amino]-4-[(methylsulfonyl)oxy]cyclohexanecarboxylic acid ethyl ester 
• 365997-34-8 ethyl (1S,3R,4S)-4-azido-3-(tert-butoxycarbonylamino)-cyclohexane-1-carboxylate 
• 1255529-35-1 ethyl (1S,3R,4R)-4-(((benzyloxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylate 
• 365998-33-0 ethyl (1S,3R,4S)-4-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]cyclohexanecarboxylate 
• 1255529-37-3 (1R,2R,4R)-2-[(Tert-butoxycarbonyl)amino]-4-[(dimethylamino)carbonyl]cyclohexylcarbamic acid benzyl ester 
• 1255529-53-3 (1S,2R,4R)-2-[(tert-butoxycarbonyl)amino]-4-[(dimethylamino)carbonyl]cyclohexylcarbamic acid benzyl ester 
• 480449-84-1 ethyl (1S,3R,4S)-4-amino-3-[(tert-butoxycarbonyl)amino]-cyclohexanecarboxylate 
• 1255529-36-2 ethyl (1R,3R,4R)-4-(((benzyloxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylate 

Relevant articles and documents

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.

Design, synthesis, and biological activity evaluation of a series of pleuromutilin derivatives with novel C14 side chains

In this work, according to the ‘me-too me-better’ design strategy, a peculiar side chain different from lefamulin at C14 position of pleuromutilin was introduced. A series of novel thioether pleuromutilin derivatives containing cyclohexane in the C14 chain was synthesized by ten-step synthesis reaction. All derivatives were characterized by Nuclear Magnetic Resonance (NMR) and High Resolution Mass Spectrometer (HRMS). Furthermore, majority of derivatives displayed moderate antibacterial activity in vitro. However, the compound 2C and 2J exhibited comparable or superior antibacterial activity to lefamulin. The summarized structure-activity relationship not only made the variety of pleuromutilin derivatives more diverse, but also provided new ideas for its design and development.

Preparation method of edoxaban intermediate

The invention discloses a preparation method of edoxaban intermediate (1S, 3R, 4R)-3-tert-butoxycarbonylamino-4-hydroxy-cyclohexanecarboxylic acid. According to the preparation method, 3-amino-4-hydroxy-cyclohexane carboxylate represented by formula IV is taken as a raw material, protective reaction with amino protection groups is carried out so as to obtain 3-tert-butoxycarbonylamino-4-hydroxy-cyclohexane carboxylate represented by formula V, enzyme catalyzed esterification resolution reaction is carried out so as to obtain optically pure (1S, 3R, 4R)-3-tert-butoxycarbonylamino-4-hydroxy-cyclohexane carboxylate represented by formula VII, and at last lithium hydroxide hydrolysis is adopted so as to obtain the (1S, 3R, 4R)-3-tert-butoxycarbonylamino-4-hydroxy-cyclohexanecarboxylic acid represented by formula VI. The preparation method possesses following advantages: operation is simple, the preparation method is green, is friendly to the environment, and is high in selectivity and lowin cost, large scale industrialized production can be realized, and it is convenient for industrial popularization.