929693-30-1

Basic information

• Product Name: carbamic acid, n-[(1r,2r,5s)-5-[(dimethylamino)carbonyl]-2-hydroxycyclohexyl]-, 1,1-dimethylethyl ester
• Synonyms: carbamic acid, n-[(1r,2r,5s)-5-[(dimethylamino)carbonyl]-2-hydroxycyclohexyl]-, 1,1-dimethylethyl ester;tert-Butyl ((1R,2R,5S)-5-(dimethylcarbamoyl)-2-hydroxycyclohexyl)carbamate;tert-butyl N-[(1R,2R,5S)-5-(dimethylcarbamoyl)-2-hydroxycyclohexyl]carbamate
• CAS NO: 929693-30-1
• Molecular Formula: C₁₄H₂₆N₂O₄
• Molecular Weight: 286.36724
• Mol File: 929693-30-1.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: carbamic acid, n-[(1r,2r,5s)-5-[(dimethylamino)carbonyl]-2-hydroxycyclohexyl]-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: carbamic acid, n-[(1r,2r,5s)-5-[(dimethylamino)carbonyl]-2-hydroxycyclohexyl]-, 1,1-dimethylethyl ester(929693-30-1)
• EPA Substance Registry System: carbamic acid, n-[(1r,2r,5s)-5-[(dimethylamino)carbonyl]-2-hydroxycyclohexyl]-, 1,1-dimethylethyl ester(929693-30-1)

Safety Data

• Hazardous Substances Data: 929693-30-1(Hazardous Substances Data)

Usage

General Description

The chemical "carbamic acid, n-[(1r,2r,5s)-5-[(dimethylamino)carbonyl]-2-hydroxycyclohexyl]-, 1,1-dimethylethyl ester" is a compound with the molecular formula C15H29N1O4. It is commonly known as tadalafil, and it is a medication used to treat erectile dysfunction and symptoms of benign prostatic hyperplasia. Tadalafil works by relaxing the blood vessels in the penis, allowing for increased blood flow and improved erectile function. Additionally, it can also relax the muscles in the prostate and bladder, which may help relieve symptoms of prostate enlargement. Tadalafil is typically taken orally and is available in tablet form. It is recommended to be taken as needed, about 30 minutes before sexual activity. Tadalafil is a phosphodiesterase type 5 inhibitor and it works by increasing the levels of cyclic guanosine monophosphate (cGMP) in the blood, leading to improved blood flow and erection. However, it should be used with caution in individuals with certain medical conditions or who are taking certain medications, and it may have potential side effects such as headache, stomach upset, muscle pain, and back pain. It is important to consult a healthcare professional before using tadalafil to ensure it is safe and appropriate for the individual.

Upstream product

• 5708-19-0 (1S)-3-cyclohexenecarboxylic acid 
• 929693-35-6 (1S,3S,6R)-N,N-dimethyl-7-oxabicyclo[4.1.0]heptane-3-carboxamide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 19914-91-1 (1RS,4RS,5RS)-4-bromo-6-oxabicyclo<3.2.1>octan-7-one 
• 4771-80-6 1,2,5,6-tetrahydrobenzoic acid 
• 67976-82-3 (1S)-3-cyclohexene-1-carboxylic acid (R)-(+)-α-methylbenzylamine salt 
• 139893-81-5 (1S,4S,5S)-4-bromo-6-oxabicyclo<3.2.1>octan-7-one 
• 929693-36-7 (1S,3R,4R)-3-amino-4-hydroxy-N,N-dimethyl cyclohexanecarboxamide 

Downstream Products

• 929693-31-2 {(1R,2R,4S)-2-[(tert-butoxycarbonyl)amino]-4-[(dimethylamino)carbonyl]cyclohexyl}methanesulfonate 
• 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 
• 480449-71-6 [14C]-Edoxaban tosylate 
• 480450-69-9 tert-butyl N-[(1R,2S,5S)-2-azido-5-[(dimethylamino)carbonyl]cyclohexyl]carbamate 
• 365998-36-3 (1S,2R,4S)-N₂-(tert-butoxycarbonyl)-4-(N,N-dimethylcarbamoyl)-1,2-cyclohexanediamine 

Relevant articles and documents

Method for preparing eteaban chiral amine intermediate (by machine translation)

The invention provides a safe and convenient method for preparing N - [(1R, 2S, 5S) -2 - amino -5 - [(dimethylamino) carbonyl] cyclohexyl] carbamic acid tert-butyl formate. The compound N - [(1R, 2R, 5S) -5 - [(dimethylamino) carbonyl] -2 - hydroxycyclohexyl] carbamic acid tert-butyl carbamate and the DBU azidate are then reacted to obtain N - [(1R, 2R, 5S) -5 - [(dimethylamino) carbonyl] cyclohexyl] carbamic acid tert-butyl formate in the presence of DBU to obtain the corresponding amino. N - [(1R, 2S, 5S) -2 - amino -2 -5 - [(dimethylamino) carbonyl] cyclohexyl] carbamic acid tert-butyl formate in the presence of a DBU to obtain the corresponding amino compound. N - 2S [(dimethylamino) carbonyl] cyclohexyl] carbamic acid tert-butyl formate 1R 5S -2 -5 . (by machine translation)

Development of an Efficient Manufacturing Process for a Key Intermediate in the Synthesis of Edoxaban

We report the development of a novel synthetic method to access a key intermediate in the synthesis of edoxaban. The main features of the new synthetic method are an improvement in the approach for the synthesis of a key chiral bromolactone, application of an interesting cyclization reaction utilizing neighboring group participation to construct a differentially protected 1,2-cis-diamine, and implementation of plug-flow reactor technology to enable the reaction of an unstable intermediate on multihundred kilogram scale. The overall yield for the preparation of edoxaban was significantly increased by implementing these changes and led to a more efficient and environmentally friendly manufacturing process.

METHOD FOR PRODUCING OPTICALLY ACTIVE DIAMINE DERIVATIVE

The problem to be solved is to provide an important intermediate for production of an FXa inhibitor. The solution thereto is a method for industrially producing a compound (1) or a compound (4), comprising: [Step 1]: adding a quaternary ammonium salt and a metal azide salt to water to prepare an aqueous solution of an azidification reagent complex comprising quaternary ammonium salt-metal azide salt, and subsequently dehydrating the aqueous solution using an aromatic hydrocarbon solvent to form a mixed solution of the azidification reagent complex comprising quaternary ammonium salt-metal azide salt and the aromatic hydrocarbon solvent with a water content of 0.2% or less; and [Step 2]: adding, to the mixed solution prepared in [Step 1], a compound (2) wherein L represents a leaving group.