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

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

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 
• 1415016-20-4 C₁₉H₂₄N₂OS 
• 711-01-3 methyl adamantane-1-carboxylate 
• 770-71-8 1-adamantanemethanol 
• 828-51-3 1-Adamantanecarboxylic acid 
• 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 

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.

Preparation method of (S)-2-(adamantane-1-yl)-2-aminoacetic acid hydrochloride

The invention discloses a preparation method of (S)-2 (adamantane-1-yl)-2-aminoacetic acid hydrochloride. The method comprises the following steps: dissolving 1-adamantane formaldehyde and (S)-(-)-tert-butylsulfinamide in dichloromethane, slowly adding a dehydrating agent and pyridine p-toluenesulfonate, reacting for 16 hours at the temperature of 20 DEG C to obtain tert-butyl sulfinyl imide; dissolving tert-butyl sulfinyl imide into dichloromethane and tetrahydrofuran, adding trimethylnitrile silane and cesium fluoride, and reacting for 16 hours at the temperature of 20 DEG C to obtain cyanide; hydrolyzing cyanide by using a hydrolysis reagent, reacting for 6 hours at the temperature of 15 DEG C, and then reacting for 16 hours at the temperature of 110 DEG C to obtain a final compound, namely(S)-2 (adamantane-1-yl)-2-aminoacetic acid hydrochloride. Thus, the technical problem that there is suitable industrial synthesis method at present is solved.

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.

Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow-Generated Diazo Compounds and Propargylated Amines

We report herein the asymmetric coupling of flow-generated unstabilized diazo compounds and propargylated amine derivatives, using a new pyridinebis(imidazoline) ligand, a copper catalyst and base. The reaction proceeds rapidly, generating chiral allenes in 10–20 minutes with high enantioselectivity (89–98 % de/ee), moderate yields and a wide functional group tolerance.

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.

Synthesis and biological evaluation of all eight stereoisomers of DPP-IV inhibitor saxagliptin

All eight stereoisomers of saxagliptin have been synthesized and evaluated for their inhibitory activity against DPP-IV. It was unambiguously confirmed that the configuration of saxagliptin was critical to potent inhibition of DPP-IV. Docking study was performed to elucidate the configuration-activity relationship of saxagliptin stereoisomers. Tyr662 and Tyr470 have been suggested as the key residues of DPP-IV interacting with the inhibitors. This work provides valuable information for further inhibitor design against DPP-IV.

A PROCESS FOR INDUSTRIAL PREPARATION OF [(S)-N-TERT BUTOXYCARBONYL-3-HYDROXY]ADAMANTYLGLYCINE

A commercially viable process for industrial preparation of [(S)-n-tert butoxycarbonyl-3-hydroxy]adamantylglycine which is a key intermediate for saxagliptin synthesis and is represented by compound of Formula-VI. The compound-VI obtained by the process of present invention has more than 99.5% HPLC purity, not more than 0.15 % of dihydroxy impurity, not more than 0.05% of isomer impurity and not more than 0.1% of any unknown impurity. Formula (VI).

PROCESS FOR PREPARING SAXAGLIPTIN AND ITS NOVEL INTERMEDIATES USEFUL IN THE SYNTHESIS THEREOF

Methods of making saxagliptin, pharmaceutically acceptable salts and hydrates thereof and intermediates thereof.

Synthesis of adamantylglycine using a diastereoselective grignard-to-nitrone addition

In contrast to amino acids with a bulky substituent like tert-leucine, adamantylglycine has so far received little attention. Here, a new, practical synthesis of adamantylglycine is described. This is based on a highly diastereoselective addition of adamantyl Grignard reagent to 2,3-O-cyclohexylideneglyceraldehyde N-benzylnitrone, mediated by the Lewis acid diethylaluminum chloride. Adamantylglycine is obtained from the nitrone in 6 steps and 28% yield as a crystalline hydrochloride with 0.5 methanol incorporated.

ADAMANTYGLYCINE-BASED INHIBITORS OF DIPEPTIDYL PEPTIDASE IV AND METHODS

Compounds are provided having the formula (I) [Chemical Structure] wherein: n is 0, 1 or 2; m is 0, 1 or 2; the sum of n + m less then or equal to 2; the dashed bonds forming a cyclopropyl ring can only be present when Y is CH; X is H or CN; Y is CH, CH2, CHF, CF2, O, S, SO, or SO2; and A is adamantyl. Further provided are methods of using such compounds for the treatment of diabetes and related diseases, and to pharmaceutical compositions containing such compounds.