155905-76-3

Basic information

• Product Name: (S)-1-Boc-azepane-2-carboxylic acid
• Synonyms: (S)-1-Boc-azepane-2-carboxylic acid;(2s)-1-[(tert-butoxy)carbonyl]azepane-2-carboxylic acid
• CAS NO: 155905-76-3
• Molecular Formula: C₁₂H₂₁NO₄
• Molecular Weight: 243.31
• EINECS: -0
• Mol File: 155905-76-3.mol
• Article Data: 9

Chemical Properties

• Melting Point: 110-112 °C
• Boiling Point: 369.0±35.0 °C(Predicted)
• Appearance: /
• Density: 1.133±0.06 g/cm3(Predicted)
• PKA: 4.03±0.20(Predicted)
• CAS DataBase Reference: (S)-1-Boc-azepane-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-Boc-azepane-2-carboxylic acid(155905-76-3)
• EPA Substance Registry System: (S)-1-Boc-azepane-2-carboxylic acid(155905-76-3)

Safety Data

• Hazardous Substances Data: 155905-76-3(Hazardous Substances Data)

Usage

General Description

(S)-1-Boc-azepane-2-carboxylic acid is a chemical compound that belongs to the class of azepane derivatives. It is a white to off-white solid with a molecular formula C11H19NO4 and a molecular weight of 233.27 g/mol. (S)-1-Boc-azepane-2-carboxylic acid is commonly used as a building block in the synthesis of various pharmaceuticals and bioactive compounds. It is also utilized in organic chemistry as a chiral auxiliary for asymmetric synthesis. Additionally, (S)-1-Boc-azepane-2-carboxylic acid possesses potential biological activities and is being studied for its potential pharmacological uses.

Upstream product

• 178112-21-5 2-hydroxymethylazepane-1-carboxylic acid 1-tert-butyl ester 
• 393827-20-8 4,5,6,7-tetrahydro-azepine-1,2-dicarboxylic acid 1-tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 66865-37-0 (S)-perhydro-2-azepinecarboxylic acid 
• 60274-60-4 1-chloro-5-iodopentane 
• 546141-53-1 (3R,4S,10aS)-3,4-diphenyloctahydro-1H-[1,4]oxazino-[4,3-a]azepin-1-one 
• 546141-52-0 (3S,5S,6R)-3-(5-Chloro-pentyl)-5,6-diphenyl-morpholin-2-one 
• 546141-51-9 tert-butyl (3S,5S,6R)-3-(5-chloropentyl)-2-oxo-5,6-diphenyl-4-morpholinecarboxylate 
• 178172-25-3 tert-butyl 2,3,4,5-tetrahydro-1H-azepine-1-carboxylate 
• 116611-45-1 (2R)-2-t-butoxycarbonylamino-3-phenylsulfonyl-1-(2-tetrahydropyranyloxy)propane 
• 124-38-9 carbon dioxide 
• 123387-52-0 N-Boc-perhydroazepine 
• 90989-12-1 (2S)-2-amino-5-hexenoic acid 
• 208522-13-8 (S)-2-N-(tert-butoxycarbonyl)-2-amino-5-hexenoic acid 

Downstream Products

• 546141-60-0 (S)-Azepane-1,2-dicarboxylic acid 2-((R)-1-benzyloxycarbonyl-ethyl) ester 1-tert-butyl ester 
• 546141-55-3 benzyl L-azepanyl-D-lactate 
• 546141-57-5 N-methyl-L-leucyl-3-phenyl-D-lactyl-N-methyl-L-leucyl-D-lactyl-N-methyl-L-leucyl-3-phenyl-D-lactyl-L-azepanyl-D-lactic acid 
• 546141-59-7 1-[2-(4-methyl-2-{methyl-[2-(4-methyl-2-{methyl-[2-(4-methyl-2-methylamino-pentanoyloxy)-3-phenyl-propionyl]-amino}-pentanoyloxy)-propionyl]-amino}-pentanoyloxy)-3-phenyl-propionyl]-azepane-2-carboxylic acid 1-benzyloxycarbonyl-ethyl ester 
• 546141-58-6 C₆₄H₉₀N₄O₁₅ 
• 66865-37-0 (S)-perhydro-2-azepinecarboxylic acid 

Relevant articles and documents

Polybasic nitrogen heterocyclic non-natural chiral amino acid and synthesis method thereof

The invention relates to a polybasic nitrogen heterocyclic non-natural chiral amino acid and a synthesis method thereof. The amino acid can be applied to molecule building for antibiotic synthesis. According to the synthesis method, 2-aminodiethyl malonate and halogenated alkanes carry out substitution reactions, cyclization reactions, and decarboxylation reactions, and the reaction products are split to obtain the polybasic nitrogen heterocyclic non-natural chiral amino acid. The provided novel synthesis method has the advantages of simple synthesis route, low cost, convenient operation, andeasiness for commercial production, the chiral purity of obtained products is high, and the application prospect is good.

NITROGEN CONTAINING BICYCLIC COMPOUNDS AND THEIR USE IN TREATMENT OF BACTERIAL INFECTIONS

Compounds of Formula (I), their preparation, and use in preventing or treating a bacterial infection are disclosed.

Asymmetrie substitutions of 2-lithiated N-boc-piperidine and N-boc-azepine by dynamic resolution

Proton abstraction of N-tertbutoxycarbonyl-piperidine (N-Boc-piperidine) with sBuLi and TMEDA provides a racemic organolithium that can be resolved using a chiral ligand. The enantiomeric organolithiums can interconvert so that a dynamic resolution occurs. Two mechanisms for promoting enantioselectivity in the products are possible. Slow addition of an electrophile such as trimethylsilyl chloride allows dynamic resolution under kinetic control (DKR). This process occurs with high enantioselectivity and is successful by catalysis with substoichiometric chiral ligand (catalytic dynamic kinetic resolution). Alternatively, the two enantiomers of this organolithium can be resolved under thermodynamic control with good enantioselectivity (dynamic thermodynamic resolution, DTR). The best ligands found are based on chiral diamino-alkoxides. Using DTR, a variety of electrophiles can be used to provide an asymmetric synthesis of enantiomerically enriched 2-substituted piperidines, including (after Boc deprotection) the alkaloid (+)-ss-conhydrine. The chemistry was extended, albeit with lower yields, to the corresponding 2-substituted sevenmembered azepine ring derivatives.