929693-31-2

Basic information

• Product Name: (1R,2R,4S)-2-[(tert-butoxycarbonyl)aMino]-4-[(diMethylaMino)carbonyl]cyclohexyl Methanesulfonate
• Synonyms: (1R,2R,4S)-2-[(tert-butoxycarbonyl)aMino]-4-[(diMethylaMino)carbonyl]cyclohexyl Methanesulfonate;Carbamic acid, N-[(1R,2R,5S)-5-[(dimethylamino)carbonyl]-2-[(methylsulfonyl)oxy]cyclohexyl]-, 1,1-dimethylethyl ester;4-(dimethylcarbamoyl)cyclohexyl methanesulfonate;Edoxaban Impurity P
• CAS NO: 929693-31-2
• Molecular Formula: C₁₅H₂₈N₂O₆S
• Molecular Weight: 364.45762
• EINECS: -0
• Mol File: 929693-31-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 546.0±50.0 °C(Predicted)
• Appearance: /
• Density: 1.21±0.1 g/cm3(Predicted)
• PKA: 11.09±0.60(Predicted)
• CAS DataBase Reference: (1R,2R,4S)-2-[(tert-butoxycarbonyl)aMino]-4-[(diMethylaMino)carbonyl]cyclohexyl Methanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R,4S)-2-[(tert-butoxycarbonyl)aMino]-4-[(diMethylaMino)carbonyl]cyclohexyl Methanesulfonate(929693-31-2)
• EPA Substance Registry System: (1R,2R,4S)-2-[(tert-butoxycarbonyl)aMino]-4-[(diMethylaMino)carbonyl]cyclohexyl Methanesulfonate(929693-31-2)

Safety Data

• Hazardous Substances Data: 929693-31-2(Hazardous Substances Data)

Usage

Uses

2-(tert-Butoxycarbonyl) Methanesulfonate Edoxaban is an impurity of Edoxaban (E555520). Edoxaban is an anticoagulant drug which acts as a direct factor Xa inhibitor.

Upstream product

• 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 
• 5708-19-0 (1S)-3-cyclohexenecarboxylic acid 
• 124-63-0 methanesulfonyl chloride 
• 929693-36-7 (1S,3R,4R)-3-amino-4-hydroxy-N,N-dimethyl cyclohexanecarboxamide 
• 929693-30-1 (1S,3R,4R)-3-[(tert-butoxycarbonyl)amino]-4-hydroxy-N,N-dimethylcyclohexanecarboxamide 

Downstream Products

• 480451-97-6 Tert-butyl {(1R,2R,5S)-2-azido-5-[(dimethylamino)carbonyl]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 
• 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

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.

PROCESS FOR THE PREPARATION OF (1S,4S,5S)-4-BROMO-6-OXABICYCLO[3.2.1] OCTAN-7-ONE

The present invention relates to an improved and industrially advantageous process for the preparation of (1S, 4S, 5S) -4-bromo-6-oxabicyclo [3.2.1] octan-7-one represented by the following formula (I) which is a key intermediate in the synthesis of edoxaban, a compound that exhibits an inhibitory effect on activated blood coagulation factor X (also referred to as activated factor X or FXa), and is useful as a preventive and/or therapeutic drug for thrombotic diseases. The process includes reacting (1S) -cyclohex-3-ene-1-carboxylic acid of formula (II) with a brominating agent selected from the group consisting of N-bromosuccinimide or 1, 3-dibromo-5, 5-dimethylhydantoin in the presence of a base selected from calcium oxide or calcium hydroxide in a solvent selected from the group comprising of dichloromethane, toluene, tetrahydrofuran, ethy1 acetate, hexanes, cyclopentyl methyl ether (CPME) or a mixture thereof to get ( 1S, 4S, 5S) -4-bromo-6-oxabicyclo [3.2.1] octan-7-one of formula (I).

PROCESS FOR PRODUCING DIAMINE DERIVATIVE

The problem to be solved is to provide an important intermediate for production of an FXa inhibitor. The solution thereto is a process for industrially producing a compound (1) represented by the following formula (1): wherein Boc represents a tert-butoxycarbonyl group.