102502-64-7

Basic information

• Product Name: (S)-2-(AdaMantan-1-yl)-2-aMinoacetic acid hydrochloride
• Synonyms: (S)-2-(AdaMantan-1-yl)-2-aMinoacetic acid hydrochloride;(S)-Adamantylglycine Hydrochloride
• CAS NO: 102502-64-7
• Molecular Formula: C₁₂H₁₉NO₂*ClH
• Molecular Weight: 245.7457
• Mol File: 102502-64-7.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: (S)-2-(AdaMantan-1-yl)-2-aMinoacetic acid hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(AdaMantan-1-yl)-2-aMinoacetic acid hydrochloride(102502-64-7)
• EPA Substance Registry System: (S)-2-(AdaMantan-1-yl)-2-aMinoacetic acid hydrochloride(102502-64-7)

Safety Data

• Hazardous Substances Data: 102502-64-7(Hazardous Substances Data)

Usage

Description

(S)-2-(AdaMantan-1-yl)-2-aMinoacetic acid hydrochloride, also known as (S)-adamantylglycine, is an organic compound derived from the adamantane structure. It is characterized by its unique cage-like structure and amine group, which contribute to its chemical properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
(S)-2-(AdaMantan-1-yl)-2-aMinoacetic acid hydrochloride is used as a key intermediate in the synthesis of saxagliptin (BMS-477118), a highly potent, long-acting, and orally active dipeptidyl peptidase IV (DPP-IV) inhibitor. (S)-2-(AdaMantan-1-yl)-2-aMinoacetic acid hydrochloride is specifically designed for the treatment of type 2 diabetes, as it helps regulate blood sugar levels by inhibiting the DPP-IV enzyme, which is responsible for the rapid degradation of insulinotropic hormones.

Upstream product

• 361441-95-4 (S)-2-(adamantan-1-yl)-2-(((R)-2-hydroxy-1-phenylethyl)amino)acetonitrile 
• 361441-97-6 (alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.1^3,7]decane-1-acetic acid 
• 182439-68-5 N-[(S)-1-Adamantan-1-yl-2-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-oxo-ethyl]-acetamide 
• 326894-41-1 (-)-(S)-[(1-adamantyl)phenylmethyl]-4-methoxyphenylamine 
• 326894-44-4 (-)-(S)-N-[(1-adamantyl)phenylmethyl]acetamide 
• 2094-74-8 1-Adamantanecarbaldehyde 
• 182439-69-6 (S)-Acetylamino-adamantan-1-yl-acetic acid 
• 1415016-20-4 C₁₉H₂₄N₂OS 
• 711-01-3 methyl adamantane-1-carboxylate 
• 770-71-8 1-adamantanemethanol 
• 828-51-3 1-Adamantanecarboxylic acid 

Downstream Products

• 909125-93-5 S-PTAd 
• 361442-01-5 tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.1³'⁷]dec-1-yl)-2-oxoethyl]carbamate 
• 361442-00-4 (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.1^3,7]decane-1-acetic acid 
• 1564266-00-7 (1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxy-1-adamantyl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile 
• 1564265-93-5 (2S,4S,5R)-2-[(2S)-2-amino-2-(3-hydroxyadamantan-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile 
• 1564265-94-6 (S)-3-hydroxyadamantylglycine-D-cis-4,5-methanoprolinenitrile 
• 1564265-93-5 saxagliptin 
• 709031-43-6 3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.1^3,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester 
• 361441-97-6 (alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.1^3,7]decane-1-acetic acid 

Relevant articles and documents

The Strecker reaction coupled to Viedma ripening: A simple route to highly hindered enantiomerically pure amino acids

The Strecker reaction is broadly used for the preparation of α-amino acids. However, control of enantioselectivity remains challenging. We here couple the Strecker reaction to Viedma ripening for the absolute asymmetric synthesis of highly sterically hindered α-amino acids. As proof-of-principle, the enantiomerically pure α-amino acids tert-leucine and α-(1-adamantyl)glycine were obtained.

Catalytic Enantioselective Intermolecular Benzylic C(sp3)?H Amination

A practical general method for asymmetric intermolecular benzylic C(sp3)?H amination has been developed by combining the pentafluorobenzyl sulfamate PfbsNH2 with the chiral rhodium(II) catalyst Rh2(S-tfptad)4. Various substrates can be used as limiting components and converted to benzylic amines with excellent yields and high levels of enantioselectivity. Additional key features for the reaction are the low catalyst loading and the ability to remove the Pfbs group under mild conditions to give NH-free benzylic amines.

Protected amino hydroxy adamantane carboxylic acid and process for its preparation

Dipeptidyl peptidase IV (DP 4) inhibiting compounds are provided. The provided compounds can be used for treating diabetes and related diseases, especially Type II diabetes, and other diseases as set out herein, employing such DP 4 inhibitor or a combination of such DP 4 inhibitor and one or more of another antidiabetic agent such as metformin, glyburide, troglitazone, pioglitazone, rosiglitazone and/or insulin and/or one or more of a hypolipidemic agent and/or anti-obesity agent and/or other therapeutic agent.