(R)-N-Boc-3-hydroxyadaMantylglycine

Base Information

• Chemical Name: (R)-N-Boc-3-hydroxyadaMantylglycine
• CAS No.: 1334321-39-9
• Molecular Formula: C17H27NO5
• Molecular Weight: 325.405
• Mol file: 1334321-39-9.mol

Synonyms:(R)-N-Boc-2-(3-hydroxyadamant-1-yl)glycine;(alphaR)-alpha-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-hydroxytricyclo[3.3.1.1(3,7)]decane-1-acetic acid;

Chemical Property of (R)-N-Boc-3-hydroxyadaMantylglycine

Chemical Property:

• Appearance/Colour: White powder
• Boiling Point: 497.3±20.0 °C(Predicted)
• PKA: 3.93±0.10(Predicted)
• PSA: 95.86000
• Density: 1.296±0.06 g/cm3 (20 oC 760 Torr)
• LogP: 2.68650
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

Boc-3-hydroxy-1-adamantyl-glycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Boc-3-hydroxy-1-adamantyl-glycine is an impurity of Saxagliptin (S143500), which is 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.

Technology Process of (R)-N-Boc-3-hydroxyadaMantylglycine

There total 7 articles about (R)-N-Boc-3-hydroxyadaMantylglycine 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: 98.0%

di-tert-butyl dicarbonate (24424-99-5) + 2-(3-hydroxy-1-adamantyl)-D-glycine (709031-29-8,709031-30-1) → N-tert-butoxycarbonyl-2-(3-hydroxy-1-adamantyl)-D-glycine (1334321-39-9)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; at 20 ℃; for 12h;

Reference yield: 42.0%

C17H27NO4 (1564266-26-7) → N-tert-butoxycarbonyl-2-(3-hydroxy-1-adamantyl)-D-glycine (1334321-39-9)

Guidance literature:

With potassium permanganate; potassium hydroxide; at 90 ℃;

DOI:10.1016/j.bmc.2013.12.061

Reference yield:

C17H27NO5*C20H24N2O2 → N-tert-butoxycarbonyl-2-(3-hydroxy-1-adamantyl)-D-glycine (1334321-39-9)

Guidance literature:

With hydrogenchloride; In water; ethyl acetate; pH=2;

DOI:10.1007/s11164-015-2398-2

upstream raw materials:

2-(R)-adamantan-1-yl-(S)-(2-hydroxy-1-phenylethylamino)acetic acid hydrochloride

C₁₇H₂₇NO₄

1-Adamantanecarbaldehyde

2-(R)-adamantan-1-yl-(S)-(2-hydroxy-1-phenylethylamino)acetonitrile

Downstream raw materials:

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.1^3,7]decane-1-acetic acid

saxagliptin

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

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