76944-95-1

Basic information

• Product Name: (S)-(2-OXO-AZEPAN-3-YL)-CARBAMIC ACID TERT-BUTYL ESTER
• Synonyms: L-(-)-3-N-BOC-AMINO-2-AZEPANONE;L(-)-N-ALPHA-BOC-AMINO-EPSILON-CAPROLACTAM;(S)-N-BOC-ALPHA-AMINO-EPSILON-CAPROLACTAME;(S)-(2-OXO-AZEPAN-3-YL)-CARBAMIC ACID TERT-BUTYL ESTER;L-(-)-N--Boc-Amino-epsilon-caprolactam;L-(-)-N-A-BOC-AMINO-EPSILON-CAPROLACTAM;L(-)-N--Boc-Amino--caprolactam;L(-)-N-A-BOC-AMINO-E-CAPROLACTAM
• CAS NO: 76944-95-1
• Molecular Formula: C₁₁H₂₀N₂O₃
• Molecular Weight: 228.29
• Mol File: 76944-95-1.mol

Chemical Properties

• Boiling Point: 417.7 °C at 760 mmHg
• Flash Point: 206.4 °C
• Appearance: /
• Density: 1.09
• Vapor Pressure: 3.47E-07mmHg at 25°C
• Refractive Index: 1.488
• Storage Temp.: 2-8°C
• PKA: 11.05±0.20(Predicted)
• CAS DataBase Reference: (S)-(2-OXO-AZEPAN-3-YL)-CARBAMIC ACID TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(2-OXO-AZEPAN-3-YL)-CARBAMIC ACID TERT-BUTYL ESTER(76944-95-1)
• EPA Substance Registry System: (S)-(2-OXO-AZEPAN-3-YL)-CARBAMIC ACID TERT-BUTYL ESTER(76944-95-1)

Safety Data

• Hazardous Substances Data: 76944-95-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-(2-OXO-AZEPAN-3-YL)-CARBAMIC ACID TERT-BUTYL ESTER is used as a building block for the synthesis of pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Synthesis:
In the agrochemical industry, (S)-(2-OXO-AZEPAN-3-YL)-CARBAMIC ACID TERT-BUTYL ESTER is used as a key intermediate in the production of various agrochemicals, including pesticides and herbicides, to enhance crop protection and yield.
Used in the Synthesis of Fine Chemicals:
(S)-(2-OXO-AZEPAN-3-YL)-CARBAMIC ACID TERT-BUTYL ESTER is employed as a reagent in the synthesis of fine chemicals, which are high-purity, specialty chemicals used in various industries such as cosmetics, fragrances, and flavorings.
Safety and Handling:
It is crucial to handle (S)-(2-OXO-AZEPAN-3-YL)-CARBAMIC ACID TERT-BUTYL ESTER with care and in accordance with proper safety protocols due to its potential hazards, ensuring the safety of both individuals and the environment.

InChI:InChI=1/C11H20N2O3/c1-11(2,3)16-10(15)13-8-6-4-5-7-12-9(8)14/h8H,4-7H2,1-3H3,(H,12,14)(H,13,15)/t8-/m0/s1

Upstream product

• 30189-36-7 N,N'-di-t-butyloxycarbonyl-(S)-lysine N-hydroxysuccinimide ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 21568-87-6 2-aminocaprolactam 
• 13734-28-6 Boc-Lys-OH 
• 1516-73-0 2-azido-1-methyl-1H-benzo[d]imidazole 
• 26081-03-8 (S)-3-aminocaprolactam hydrochloride 
• 2483-46-7 Boc-Lys(Boc)-OH 
• 2389-45-9 Boc-Lys(Z)-OH 
• 1055423-27-2 (3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]hexahydro-2-oxo-1H-azepine-1-carboxylic acid phenylmethyl ester 

Downstream Products

• 186261-92-7 3-((S)-3-tert-Butoxycarbonylamino-2-oxo-azepan-1-yl)-propionic acid benzyl ester 
• 93961-02-5 (S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-oxo-hexahydro-1H-azepine-1-acetic acid,phenylmethyl ester 
• 361385-59-3 (1-biphenyl-4-ylmethyl-2-oxo-azepan-3-yl)-carbamic acid tert-butyl ester 
• 380629-65-2 (S)-1-benzyl-2-oxo-3-(tert-butoxycarbonylamino)-azepine 
• 258870-43-8 (S)-1-phenyl-2-oxo-3-(tert-butoxycarbonylamino)-azepine 
• 93961-03-6 (S)-3-Amino-2-oxo-hexahydro-1H-azepine-1-acetic acid, phenylmethyl ester 
• 174960-89-5 ((S)-2-Oxo-3-phenylmethanesulfonylamino-azepan-1-yl)-acetic acid benzyl ester 
• 174960-90-8 (3S)-hexahydro-2-oxo-3-[[(phenylmethyl)sulfonyl]amino]-1H-azepine-1-acetic acid 
• 368426-13-5 ((S)-3-Benzenesulfonylamino-2-oxo-azepan-1-yl)-acetic acid 
• 174960-93-1 ((S)-3-Benzenesulfonylamino-2-oxo-azepan-1-yl)-acetic acid benzyl ester 
• 368426-15-7 [(S)-3-(2,5-Dimethoxy-benzenesulfonylamino)-2-oxo-azepan-1-yl]-acetic acid 

Relevant articles and documents

(S)-2-AMINO-6-((3-AMINOPROPYL)AMINO)HEXANOIC ACID (APL) FOR USE IN THE TREATMENT OF NON-ALCOHOLIC STEATOHEPATITIS (NASH), LIVER INFLAMMATION, HEPATOCELLULAR BALLOONING, LIVER FIBROSIS AND STEATOSIS

(S)-2-amino-6-((3-aminopropyl)amino)hexanoic acid (APL) for use in the treatment of non-alcoholic steatohepatitis (NASH), liver inflammation, hepatocellular ballooning, liver fibrosis and steatosis.

Protein synthesis with conformationally constrained cyclic dipeptides

We have synthesized several conformationally constrained dipeptide analogues as possible substrates for incorporation into proteins. These have included three cyclic dipeptides formed from Boc derivatives of 2,4-diaminobutyric acid, ornithine and lysine, having 5-, 6-, and 7-membered lactam rings, respectively. These dipeptides were used to activate a suppressor tRNA transcript, the latter of which had been prepared by in vitro transcription. Using modified E. coli ribosomes described previously, these activated suppressor tRNAs enabled the incorporation of the three cyclic dipeptides into dihydrofolate reductase (DHFR) at positions 18 and 49. The suppression yields increased with increasing lactam ring size and were found to proceed in suppression yields ranging from 3.4 to 8.9% at two different protein sites for the 5-, 6- and 7-membered lactam dipeptides. The greater facility of incorporation of the 7-membered lactam prompted us to prepare two 7-membered cyclic acylhydrazides (4 and 5) by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI)-mediated cyclization of amino acids having selectively protected hydrazine functional groups in their side chains. In common with the lactam dipeptides, acylhydrazide dipeptides 4 and 5 could be used to activate the same suppressor tRNA transcript and to incorporate the cyclic dipeptides into DHFR. They were incorporated into the same two DHFR sites in suppression yields ranging from 8.3 to 11.2%.

COMPOSITIONS AND METHODS FOR TREATMENT OF INSULIN RESISTANCE

In certain embodiments, this disclosure relates to methods of treating or preventing type 2 diabetes, pre-diabetes and conditions characterized by an increase in the levels of AIC, glucose, insulin, homeostasis model of assessment of insulin resistance (HOMA-IR), oxidative stress in adipose tissue, and earbonvlation of GLUT4 comprising administering an effective amount of a compound of Formula I-III as described herein, to a subject in need thereof.

COMPOSITIONS AND METHODS FOR TREATMENT OF INSULIN RESISTANCE

Compounds of Formula (I), and pharmaceutically effective salts thereof; wherein R1 - R14, m, n, o, p, q and r are as defined herein, are provided for treatment of for increasing insulin sensitivity, reducing insulin resistance, preventing insulin resistance and treating insulin resistance disorders.

RIBOSOME-MEDIATED INCORPORATION OF PEPTIDES AND PEPTIDOMIMETICS

Modified ribosomes that were selected using a dipeptidyl-puromycin aminonucleoside are used to mediate site-specific incorporation of one or more peptides and peptidomimetics into protein in a cell free translation system. In addition, new fluorescent dipeptidomimetics have been synthesized and incorporated into proteins, as well as modified proteins containing one or more non-naturally occurring dipeptides.

Water compatible photoarylation of amino acids and peptides

A novel photoarylation of amino acids and peptides is described, which tolerates the presence of water. Irradiation of Boc-protected amino acids in the presence of N-protected 2-azidobenzimidazoles leads to selective arylation of carboxy termini or side chains. The new reaction also works for peptides. Irradiation of the nonapeptide H-SPSYVYHQF-OH also resulted in selective arylation of the tyrosine side chains, as indicated by ESI-MS/MS fragmentation. Chemo- and regioselectivity could add the title reaction to the repertoire of photoaffinity labeling methods.

SUBSTITUTED ADIPIC ACID AMIDES AND USES THEREOF

The present invention provides compounds of Formula (I), or a pharmaceutically acceptable salt thereof, wherein A is a five to eight membered monocyclic or a nine to twelve membered bicyclic heterocyclic ring, as further defined herein; Y is S, CH2, or CH; Z is CH or N; R7 and R9 are hydrogen or (C1-C6)alkyl; R2 is (C1 C6)alkoxy, OH, CN, (C1-C6)alkyl, halogen, or CF3; r and s are 0, 1, or 2; and R1 and R3 are as further defined herein. These compounds are agonists, partial agonists and/or modulators of the NPY4 receptor and may be used for the treatment and prophylaxis of obesity, food intake, and other diseases and conditions modulated by the NPY4 receptor.

Efficient, solventless N-Boc protection of amines carried out at room temperature using sulfamic acid as recyclable catalyst

A simple, rapid, and efficient protocol for the chemoselective N-Boc protection of amines using sulfamic acid as catalyst is described. N-Boc protection of various structurally diverse aliphatic, aromatic, alicyclic, and heterocyclic amines (1°, 2°, 3°) was carried out with (Boc)2O using sulfamic acid as catalyst (5 mol %) at room temperature under solventless conditions. The advantages of this method are simplicity, shorter reaction times (1-15 min), a cost-effective catalyst, and excellent isolated yields (90-100%); it is also environmentally benign. Moreover, the combined use of ultrasound and sulfamic acid achieves a synergic effect that is especially marked in the N-Boc protection of deactivated (sterically hindered and electron-deficient) amines. The catalyst possesses distinct advantages: ease of handling, cleaner reactions, high activity, and excellent chemoselectivity.

Synthesis of a hexahydropyrimido[1,2-a]azepine-2-carboxamide derivative useful as an HIV integrase inhibitor

The hexahydropyrimido[1,2-a]azepine-2-carboxamide derivative 1 could be obtained by three synthetic strategies, which allowed access to multigram amounts of material of high purity and ee. Two strategies involved alternative approaches to the bicyclic pyrimidone core, with the most efficient one being a two-step sequence from commercially available starting materials exploiting a little precedented cyclisation reaction. The remaining steps to 1 included an efficient crystallisation of an intermediate as a single stereoisomer. An alternative strategy employing a chiral starting material led to products of low optical purity but allowed the assignment of the configuration of the stereogenic centre of 1.

P38 INHIBITORS AND METHODS OF USE THEREOF

Compounds of formula (I): in which A, B, X, Ar1, R8 and R4 have any of the meanings given in the specification, are inhibitors of p38 useful in the treatment and prevention of various disorders mediated by p38.