681282-72-4

Basic information

• Product Name: (S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid
• Synonyms: (S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid
• CAS NO: 681282-72-4
• Molecular Weight: 341.404
• Mol File: 681282-72-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 534.7±35.0 °C(Predicted)
• Density: 1.406±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid(681282-72-4)
• EPA Substance Registry System: (S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid(681282-72-4)

Safety Data

• Hazardous Substances Data: 681282-72-4(Hazardous Substances Data)

Usage

Uses

Boc-3,5-dihydroxy-1-adamantyl-L-glycine is a reactant in the synthesis of Saxagliptin (S143500), a potent and selective reversible inhibitor of dipeptidyl peptidase-4, which is being developed for the treatment of type 2 diabetes. It is absorbed rapidly after oral administration and has a pharmacokinetic profile compatible with once daily dosing.

Upstream product

• 361442-00-4 (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.1^3,7]decane-1-acetic acid 
• 95853-35-3 (S)-(+)-β-amino-1-adamantaneacetic acid 
• 711-01-3 methyl adamantane-1-carboxylate 
• 2094-74-8 1-Adamantanecarbaldehyde 
• 828-51-3 1-Adamantanecarboxylic acid 
• 770-71-8 1-adamantanemethanol 
• 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 

Relevant articles and documents

The synthesis of 14C-labeled, 13CD 2-labeled saxagliptin, and its 13CD2-labeled 5-hydroxy metabolite

14C-labeled saxagliptin, 13CD2-labeled saxagliptin, and its 13CD2-labeled 5-hydroxy metabolite were synthesized to further support development of the compound for biological studies. This paper describes new syntheses leading to the desired compounds. A total of 3.0 mCi of 14C-labeled saxagliptin was obtained with a specific activity of 53.98 μCi/mg (17.13 mCi/mmol). The radiochemical purity determined by HPLC was 99.29%, and the overall radiochemical yield was 3.0% based upon 100 mCi of [14C]CH2I2 starting material. By following similar synthetic routes, 580.0 mg of 13CD2-labeled saxagliptin and 153.1 mg of 13CD2-labeled 5-hydroxysaxagliptin metabolite were prepared. Copyright

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.