(2S)-2-Amino-2-(3-hydroxyadamantan-1-yl)acetic acid

Base Information

• Chemical Name: (2S)-2-Amino-2-(3-hydroxyadamantan-1-yl)acetic acid
• CAS No.: 709031-29-8
• Molecular Formula: C12H19NO3
• Molecular Weight: 225.28
• DSSTox Substance ID: DTXSID50437544
• Mol file: 709031-29-8.mol

Synonyms:(2S)-2-Amino-2-(3-hydroxyadamantan-1-yl)acetic acid;709031-29-8;3-Hydroxy-1-adamantyl-D-glycine;(2S)-2-amino-2-(3-hydroxy-1-adamantyl)acetic Acid;(2S)-2-Amino-2-(3-hydroxyadamantan-1-yl)aceticacid;(alphaS)-alpha-amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid;SCHEMBL2110155;DTXSID50437544;ZOFWFAZCJJJYCE-WNMKMJAUSA-N;AKOS016011119;CS-0112272;(2S)-Amino(3-hydroxy-1-adamantanyl)acetic acid;A853178;(S)-amino-(3-hydroxy -adamantan-1-yl)-acetic acid;(S)-amino-(3-hydroxy-adamantan-1-yl)-acetic acid;2-(3-hydroxy-1-adamantyl)-(2s)-aminoethanoic acid

Chemical Property of (2S)-2-Amino-2-(3-hydroxyadamantan-1-yl)acetic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.645
• Boiling Point: 401.967 °C at 760 mmHg
• PKA: 2.36±0.10(Predicted)
• Flash Point: 196.903 °C
• PSA: 83.55000
• Density: 1.409 g/cm³
• LogP: 1.42990
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: DMSO (Slightly, Heated), Water (Sparingly)
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 225.13649347
• Heavy Atom Count: 16
• Complexity: 327

Purity/Quality:

99% ^*data from raw suppliers

3-Hydroxy-1-adamantyl-D-glycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2CC3(CC1CC(C2)(C3)O)C(C(=O)O)N
• Isomeric SMILES: C1C2CC3(CC1CC(C2)(C3)O)[C@@H](C(=O)O)N
• Uses: 3-Hydroxy-1-adamantyl-D-glycine is a non-proteinogenic amino acid and a key intermediate required for the synthesis of Saxagliptin (S143500).

Technology Process of (2S)-2-Amino-2-(3-hydroxyadamantan-1-yl)acetic acid

There total 41 articles about (2S)-2-Amino-2-(3-hydroxyadamantan-1-yl)acetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

3-hydroxy-α-oxotricyclo [3.3.1.13,7]decane-1-acetic acid (709031-28-7) → (αS)-α-amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid (709031-29-8,709031-30-1)

Guidance literature:

With NAD; ammonium formate; diothiothreitol; In ammonium hydroxide; at 40 ℃; for 38h; pH=8.0; Enzymatic reaction;

DOI:10.1002/adsc.200700013

Reference yield: 93.56%

C20H27NO3 → (αS)-α-amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid (709031-29-8,709031-30-1)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; acetic acid; In methanol; dichloromethane; at 35 ℃; for 4h; under 4500.45 Torr; Pressure; Large scale;

Reference yield: 90.0%

α-bromo-3-hydroxy-1-adamantyl acetic acid → 3-hydroxy-1-adamantyl-glycine (709031-29-8,709031-30-1)

Guidance literature:

With ammonia; In water; at 65 ℃; for 16h;

upstream raw materials:

3-hydroxy-α-oxotricyclo [3.3.1.1^3,7]decane-1-acetic acid

3-hydroxytricyclo[3.3.1.1³'⁷]decane-1-carbaldehyde

C₁₉H₂₄N₂O₂S

C₁₉H₂₅NO₄S

Downstream raw materials:

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

Refernces

• 1、 -. "Synthetic method of saxagliptin intermediate". . . Retrieved 2021/11/21.
• 2、 -. "A process for preparing hydroxy adamantane glycine derivatives". . . Retrieved 2017/07/14.