709031-29-8

Basic information

• Product Name: (alphaS)-alpha-Amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
• Synonyms: (alphaS)-alpha-Amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid;3-Hydroxy-1-adamantyl-D-glycine;3-Hydroxy-1-adaMantyl-D-glyci;3-Hydroxy-1-adaMantyl-D-glycine CAS：709031-29-8;(2S)-2-AMino-2-(3-hydroxyadaMantan-1-yl)acetic acid;Saxagliptin INT 1;Tricyclo[3.3.1.13,7]decane-1-acetic acid,alpha-amino-3-hydroxy-,(alphaS)-
• CAS NO: 709031-29-8
• Molecular Formula: C12H19NO3
• Molecular Weight: 225.28416
• EINECS: 1308068-626-2
• Mol File: 709031-29-8.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 401.967 °C at 760 mmHg
• Flash Point: 196.903 °C
• Appearance: /
• Density: 1.409
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.645
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: DMSO (Slightly, Heated), Water (Sparingly)
• PKA: 2.36±0.10(Predicted)
• CAS DataBase Reference: (alphaS)-alpha-Amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (alphaS)-alpha-Amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid(709031-29-8)
• EPA Substance Registry System: (alphaS)-alpha-Amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid(709031-29-8)

Safety Data

• Hazardous Substances Data: 709031-29-8(Hazardous Substances Data)

Usage

Uses

3-Hydroxy-1-adamantyl-D-glycine is a non-proteinogenic amino acid and a key intermediate required for the synthesis of Saxagliptin (S143500).

InChI:InChI=1/C12H19NO3/c13-9(10(14)15)11-2-7-1-8(3-11)5-12(16,4-7)6-11/h7-9,16H,1-6,13H2,(H,14,15)/t7?,8?,9-,11?,12?/m1/s1

Upstream product

• 345969-40-6 2-(3-bromo-1-adamantyl)-D-glycine 
• 150-30-1 Phenylalanine 
• 156-06-9 2-oxo-3-(phenyl)propionic acid 
• 59768-71-7 2-(adamantan-1-yl)-2-aminoacetic acid 
• 16091-98-8 oxo-tricyclo[3.3.1.1^3,7]decan-1-yl-acetic acid 
• 709031-28-7 3-hydroxy-α-oxotricyclo [3.3.1.1^3,7]decane-1-acetic acid 
• 1660-04-4 1-acetyladamantane 
• 2094-74-8 1-Adamantanecarbaldehyde 
• 770-71-8 1-adamantanemethanol 

Downstream Products

• 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 

Relevant articles and documents

A facile synthesis of saxagliptin intermediate N-Boc-3-hydroxyadamantylglycine

Commercial-scale synthesis of (S)-N-Boc-3-hydroxyadamantylglycine (I), which is the key intermediate of saxagliptin, can be achieved from 2-(3-hydroxy-1-adamantyl)-2-oxoacetic acid (6) by reductive amination with phenylalanine dehydrogenase. The biological enzyme used in the original medicinal chemistry route is expensive and not easily obtained, making it unsuitable for further development. In this work, we developed a conventional chemical approach to give the corresponding oxime from oxoacetic acid followed by reduction of oxime and protected amino with (Boc)2O to afford the racemic mixture of N-Boc-3-hydroxyadamantylglycine (III). Utilizing this route, N-Boc-3-hydroxyadamantylglycine was prepared in six linear chemical steps with 38 % overall yield.

Synthetic method of saxagliptin intermediate (by machine translation)

(1) The compound 1 is reacted under the action of sodium ethoxide in a substitution reaction under the action of sodium ethoxide to form compound 2 by stirring and refluxing 2 under the action of sodium ethoxide to form compound 2; (8 hours) compound 3 is reacted 3 at room temperature under the alkaline condition by adding L - arginine to obtain a salvildagliptin intermediate, compound 3) and liquid bromine under the action of sodium ethoxide and then adding L-arginine under the action of sodium ethoxide under the action of sodium ethoxide and then 8 hours adding L-arginine 4 under the 4 action of 4 sodium ethoxide 12 hours. Raw materials and reagents are cheap and easily available, the reaction operation is simple, the reaction conditions are mild, the yield is high, the quality is good, the resolution end product can reach 99% ee values, and the requirements of drug intermediates are met. (by machine translation)

Intermediate sand Geleg sandbank, its salt, its preparation process and its use (by machine translation)

The invention discloses a saxagliptin intermediate, its salt, preparation method and application. The preparation method for the compound 1 or its salt comprises the step of: subjecting an intermediate compound 2 to reduction reaction at a reaction temperature ranging from -15DEG C to 45DEG C in a solvent under the effects of a reducing agent and an organic acid to obtain an intermediate compound 1 or its salt, with the reducing agent being a borohydride of an alkali metal. The preparation method for the compound 2 comprises the step of: under the protection of an inert gas and the action of the organic acid, reacting a compound B with a compound F in a solvent. The invention also discloses application of the intermediate compound or its salt in preparation of saxagliptin. The saxagliptin intermediate involved in the invention has the advantages of easy preparation, simple operation, mild condition, low cost and environmental friendliness, and can meet the requirements of industrial production. (formula 1 and formula 2).