(2S)-2-[(3R,5S)-3,5-dihydroxy-1-adamantyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid

Base Information

• Chemical Name: (2S)-2-[(3R,5S)-3,5-dihydroxy-1-adamantyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid
• CAS No.: 681282-72-4
• Molecular Formula: C₁₇H₂₇NO₆
• Molecular Weight: 341.404
• DSSTox Substance ID: DTXSID90466333
• Wikidata: Q82292873
• Mol file: 681282-72-4.mol

Synonyms:(2S)-2-[(3R,5S)-3,5-dihydroxy-1-adamantyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid;681282-72-4;TRI048;DTXSID90466333

Chemical Property of (2S)-2-[(3R,5S)-3,5-dihydroxy-1-adamantyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid

Chemical Property:

• Boiling Point: 534.7±35.0 °C(Predicted)
• Density: 1.406±0.06 g/cm3(Predicted)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 341.18383758
• Heavy Atom Count: 24
• Complexity: 550

Purity/Quality:

99% ^*data from raw suppliers

Boc-3,5-dihydroxy-1-adamantyl-L-glycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(C(=O)O)C12CC3CC(C1)(CC(C3)(C2)O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](C(=O)O)C12CC3C[C@](C1)(C[C@@](C3)(C2)O)O
• 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.

Technology Process of (2S)-2-[(3R,5S)-3,5-dihydroxy-1-adamantyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid

There total 9 articles about (2S)-2-[(3R,5S)-3,5-dihydroxy-1-adamantyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]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: 51.0%

(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid (361441-97-6) → (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid (361442-00-4) + (S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid (681282-72-4)

Guidance literature:

With potassium hydroxide; potassium permanganate; at 60 - 90 ℃; for 1.5h;

DOI:10.1021/jm050261p

Reference yield: 25.0%

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid (361442-00-4) → (S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid (681282-72-4)

Guidance literature:

With potassium permanganate; potassium hydroxide; In water; at 60 - 85 ℃; for 1.5h;

DOI:10.1002/jlcr.3179

Reference yield:

(S)-2-(adamantan-1-yl)-2-(((R)-2-hydroxy-1-phenylethyl)amino)acetonitrile (361441-95-4) → (S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid (681282-72-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / aq. HCl; AcOH / 18 h / 80 °C

2: H₂; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr

3: 4.07 g / K₂CO₃ / dimethylformamide / 19 h

4: 17 percent / KMnO₄; aq. KOH / 1.5 h / 60 - 90 °C

With hydrogenchloride; potassium hydroxide; potassium permanganate; hydrogen; potassium carbonate; acetic acid; palladium dihydroxide; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm050261p

upstream raw materials:

(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.1^3,7]decane-1-acetic acid

(S)-2-(adamantan-1-yl)-2-(((R)-2-hydroxy-1-phenylethyl)amino)acetonitrile

1-adamantanemethanol

1-Adamantanecarboxylic acid