161511-90-6

Basic information

• Product Name: (R)-1-(TERT-BUTOXYCARBONYL)-2-AZETIDINEMETHANOL
• Synonyms: 1-Azetidinecarboxylicacid, 2-(hydroxymethyl)-, 1,1-dimethylethyl ester, (2R)-;(R)-2-HYDROXYMETHYL-AZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;(R)-1-(TERT-BUTOXYCARBONYL)-2-AZETIDINEMETHANOL;(R)-1-BOC-2-AZETIDINEMETHANOL;(R)-1-Boc-2-azetidinemeth...;(R)-tert-butyl 2-(hydroxyMethyl)azetidine-1-carboxylate;(R)-1-(tert-Butoxycarbonyl)-2-azetidineMethanol;tert-butyl (2R)-2-(hydroxymethyl)azetidine-1-carboxylate
• CAS NO: 161511-90-6
• Molecular Formula: C₉H₁₇NO₃
• Molecular Weight: 187.24
• Product Categories: Azetidines;Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Simple 4-Membered Ring Compounds;Synthetic Organic Chemistry
• Mol File: 161511-90-6.mol

Chemical Properties

• Boiling Point: 270.349 °C at 760 mmHg
• Flash Point: 117.303 °C
• Appearance: /
• Density: 1.116 g/cm³
• Refractive Index: 1.4580-1.4620
• Storage Temp.: 2-8°C
• PKA: 14.77±0.10(Predicted)
• CAS DataBase Reference: (R)-1-(TERT-BUTOXYCARBONYL)-2-AZETIDINEMETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-(TERT-BUTOXYCARBONYL)-2-AZETIDINEMETHANOL(161511-90-6)
• EPA Substance Registry System: (R)-1-(TERT-BUTOXYCARBONYL)-2-AZETIDINEMETHANOL(161511-90-6)

Safety Data

• Hazardous Substances Data: 161511-90-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-1-(TERT-BUTOXYCARBONYL)-2-AZETIDINEMETHANOL is used as a key intermediate in the synthesis of various pharmaceutical compounds, particularly for the development of oral analgesics. Its unique structure allows for efficient asymmetric synthesis, which is crucial in creating effective and selective pain-relieving medications.
Used in Pain Management Research:
In the field of pain management, (R)-1-(TERT-BUTOXYCARBONYL)-2-AZETIDINEMETHANOL has been utilized to study the structure-activity relationship of (azetidinylmethoxy)chloropyridine derivatives. This research helps in understanding the molecular interactions and mechanisms behind the analgesic effects of these compounds, ultimately leading to the development of more potent and safer pain-relieving drugs.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 95729-87-6 benzyl (2R)-4-oxoazetidine-2-carboxylate 
• 209329-11-3 (2R)-2-azetidinylmethanol 
• 228857-58-7 (R)-N-(tert-butoxycarbonyl)azetidine-2-carboxylic acid 

Downstream Products

• 228867-09-2 (R)-tert-butyl 2-((5-bromopyridin-3-yloxy)methyl)azetidine-1-carboxylate 
• 1434047-88-7 (R)-tert-butyl 2-((5-(phenylethynyl)pyridin-3-yloxy)methyl)azetidine-1-carboxylate 
• 887626-82-6 (R)-tert-butyl 2-(aminomethyl)azetidine-1-carboxylate 
• 935668-80-7 (R)-azetidin-2-ylmethanol hydrochloride 
• 1217413-72-3 tert-butyl (2R)-2-{[2-({(3E)-5-tert-butyl-1-methyl-2-[(2R)-tetrahydrofuran-2-ylmethyl]-1,2-dihydro-3H-pyrazol-3-ylidene}carbamoyl)-4-(trifluoromethyl)phenoxy]methyl}azetidine-1-carboxylate 
• 1215230-32-2 tert-butyl (2R)-2-{[2-{[(2Z)-5-tert-butyl-3-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3-thiazol-2(3H)-ylidene]carbamoyl}-4-(trifluoromethyl)phenoxy]methyl}azetidine-1-carboxylate 
• 209328-49-4 (R)-2-(toluene-4-sulfonyloxymethyl)azetidinecarboxylic acid tert-butyl ester 
• 1005756-63-7 (R)-tert-butyl 2-(azidomethyl)azetidine-1-carboxylate 

Relevant articles and documents

Two Scalable Syntheses of (S)-2-Methylazetidine

Two orthogonal routes for preparing (S)-2-methylazetidine as a bench stable, crystalline (R)-(-)-CSA salt are presented. One route features the in situ generation and cyclization of a 1,3-bis-triflate to form the azetidine ring, while the second route inv

Discovery of LOU064 (Remibrutinib), a Potent and Highly Selective Covalent Inhibitor of Bruton's Tyrosine Kinase

Bruton's tyrosine kinase (BTK), a cytoplasmic tyrosine kinase, plays a central role in immunity and is considered an attractive target for treating autoimmune diseases. The use of currently marketed covalent BTK inhibitors is limited to oncology indications based on their suboptimal kinase selectivity. We describe the discovery and preclinical profile of LOU064 (remibrutinib, 25), a potent, highly selective covalent BTK inhibitor. LOU064 exhibits an exquisite kinase selectivity due to binding to an inactive conformation of BTK and has the potential for a best-in-class covalent BTK inhibitor for the treatment of autoimmune diseases. It demonstrates potent in vivo target occupancy with an EC90 of 1.6 mg/kg and dose-dependent efficacy in rat collagen-induced arthritis. LOU064 is currently being tested in phase 2 clinical studies for chronic spontaneous urticaria and Sjoegren's syndrome.

CHEMICAL COMPOUNDS AS H-PGDS INHIBITORS

A compound of formula (I) wherein R1, R2, R3, R4, X, Y, and A are as defined herein. The compounds of the present invention are inhibitors of hematopoietic prostaglandin D synthase (H-PGDS) and can be useful in the treatment of Duchenne muscular dystrophy. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting H-PGDS activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

Discovery of Pyrrolidine-Containing GPR40 Agonists: Stereochemistry Effects a Change in Binding Mode

A novel series of pyrrolidine-containing GPR40 agonists is described as a potential treatment for type 2 diabetes. The initial pyrrolidine hit was modified by moving the position of the carboxylic acid, a key pharmacophore for GPR40. Addition of a 4-cis-CF3 to the pyrrolidine improves the human GPR40 binding Ki and agonist efficacy. After further optimization, the discovery of a minor enantiomeric impurity with agonist activity led to the finding that enantiomers (R,R)-68 and (S,S)-68 have differential effects on the radioligand used for the binding assay, with (R,R)-68 potentiating the radioligand and (S,S)-68 displacing the radioligand. Compound (R,R)-68 activates both Gq-coupled intracellular Ca2+ flux and Gs-coupled cAMP accumulation. This signaling bias results in a dual mechanism of action for compound (R,R)-68, demonstrating glucose-dependent insulin and GLP-1 secretion in vitro. In vivo, compound (R,R)-68 significantly lowers plasma glucose levels in mice during an oral glucose challenge, encouraging further development of the series.

Substituted Disulfonamide Compounds

Substituted disulfonamide compounds corresponding to formula I: In which R1, R2, R3, R4a, R4b, R5a, R5b, R8, R9a, R9b, R10, R11, a, b, s, t and A have defined meanings, pharmaceutical compositions containing one or more such compounds, processes for preparing such compounds, and a method of using such compounds for the treatment or inhibition of pain and/or other conditions mediated by the bradykinin receptor 1 (BR1).

CERTAIN CHEMICAL ENTITIES, COMPOSITIONS, AND METHODS

Chemical entities that modulate smooth muscle myosin and/or non-muscle myosin, and chemical entities, pharmaceutical compositions and methods of treatment of diseases and conditions associated with smooth muscle myosin and/or non-muscle myosin are described.

3-Pyridyl enantiomers and their use as analgesics

The present invention relates to a method of controlling pain in mammals, including humans, comprising administering to a mammal or patient in need of treatment thereof selected compounds of formula I: STR1 or a pharmaceutically acceptable salt thereof. The invention further relates to selected (R) and (S) compounds of formula I above which are useful as analgesics as well as neuronal cell death preventors and anti-inflammatories.

3-pyridyloxymethyl heterocyclic ether compounds useful in controlling neurotransmitter release

Novel heterocyclic ether compounds of the formula: STR1 wherein n, *, R1, R2, R3 and y are specifically defined, or pharmaceutically acceptable salts or prodrugs thereof, which are useful in selectively controlling neurotransmitter release; therapeutically-effective pharmaceutical compositions of these compounds; and use of said compositions to selectively control neurotransmitter release in mammals.

Efficient asymmetric synthesis of ABT-594; a potent, orally effective analgesic

A concise asymmetric synthesis of (R)-2-chloro-5-(2- azetidinylmethoxy)pyridine (ABT-594) is presented in which the key intermediate t-butoxycarbonyl protected (2R)-azetidinylalcohol is obtained in three steps from the dibenzyl ester of D-aspartic acid in 44% yield and >99% ee.