(2S)-2-((tert-Butoxycarbonyl)amino)-2-(3-hydroxyadamantan-1-yl)acetic acid

Base Information

• Chemical Name: (2S)-2-((tert-Butoxycarbonyl)amino)-2-(3-hydroxyadamantan-1-yl)acetic acid
• CAS No.: 361442-00-4
• Molecular Formula: C17H27NO5
• Molecular Weight: 325.405
• Hs Code.: 2924199090
• European Community (EC) Number: 700-361-0
• DSSTox Substance ID: DTXSID60957561
• Mol file: 361442-00-4.mol

Synonyms:361442-00-4;(2S)-2-((tert-Butoxycarbonyl)amino)-2-(3-hydroxyadamantan-1-yl)acetic acid;BOC-3-Hydroxy-1-adamantyl-D-Glycine;(S)-N-Boc-3-hydroxyadamantylglycine;(2S)-[(tert-Butoxycarbonyl)amino](3-hydroxytricyclo[3.3.1.13,7]decan-1-yl)ethanoic acid;MFCD16660445;(2S)-((tert-Butoxycarbonyl)amino)(3-hydroxytricyclo(3.3.1.1 3,7)dec-1-yl)acetic acid;EC 700-361-0;(S)-2-(Boc-amino)-2-(3-hydroxy-1-adamantanyl)acetic Acid;SCHEMBL2110140;C17H27NO5;DTXSID60957561;(2S)-2-{[(tert-butoxy)carbonyl]amino}-2-(3-hydroxyadamantan-1-yl)acetic acid;UKCKDSNFBFHSHC-ZEJPWUNMSA-N;(alphaS)-alpha-[[(1,1-DiMethylethoxy)carbonyl]aMino]-3-hydroxytricyclo [3.3.1.13,7]decane-1-acetic acid;BCP02491;(2S)-2-((tert-Butoxycarbonyl)amino)-2-(3-hydroxyadamantan-1-yl)aceticacid;AKOS016843568;DS-4349;EX-7794;(2S)-2-(3-hydroxy-1-adamantyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic Acid;BOC-3HYDROXY-1ADMANTYL-D- Glycine;CS-0135316;tert-butoxycarbonylamino-(3-hydroxyadamantan-1-yl)acetic acid;(S)-2-((tert-Butoxycarbonyl)amino)-2-((1r,3R,5R,7S)-3-hydroxyadamantan-1-yl)acetic acid;(2S)-[(tert-Butoxycarbonyl)amino]-2-(3-hydroxytricyclo[3.3.1.1(3,7)]dec-1-yl)acetic Acid;(alphaS)-alpha-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid;(alphaS)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid;(alphaS)-alpha[[(1,1-dimethylethoxy)carbonyl]amino]-3-hydroxytricyclo[3.3.1.1 3,7]decane-1-acetic acid;(alphaS)-alpha[[(1,1-dimethylethoxy)carbonyl]amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Chemical Property of (2S)-2-((tert-Butoxycarbonyl)amino)-2-(3-hydroxyadamantan-1-yl)acetic acid

Chemical Property:

• Boiling Point: 497.253 °C at 760 mmHg
• PKA: 3.93±0.10(Predicted)
• Flash Point: 254.53 °C
• PSA: 95.86000
• Density: 1.296 g/cm³
• LogP: 2.68650
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly, Heated), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 325.18892296
• Heavy Atom Count: 23
• Complexity: 510

Purity/Quality:

99% ^*data from raw suppliers

Boc-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: CC(C)(C)OC(=O)NC(C(=O)O)C12CC3CC(C1)CC(C3)(C2)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](C(=O)O)C12CC3CC(C1)CC(C3)(C2)O
• Uses: Boc-3-hydroxy-1-adamantyl-D-glycine is used in the preparation of a Saxagliptin intermediate.

Technology Process of (2S)-2-((tert-Butoxycarbonyl)amino)-2-(3-hydroxyadamantan-1-yl)acetic acid

There total 52 articles about (2S)-2-((tert-Butoxycarbonyl)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: 98.1%

N-tert-butoxycarbonyl-2-(3-hydroxy-1-adamantyl)-D-glycine ethyl ester → (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid (361442-00-4)

Guidance literature:

With water; sodium hydroxide; In ethanol; at 18 - 65 ℃; for 2h;

Reference yield: 98.0%

(αS)-α-amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid (709031-29-8,709031-30-1) + di-tert-butyl dicarbonate (24424-99-5) → (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid (361442-00-4)

Guidance literature:

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

Reference yield: 56.0%

N-tert-butoxycarbonyl-3-hydroxy-1-adamantaneglycine → (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid (361442-00-4)

Guidance literature:

With (1R,2S)-2-Amino-1,2-diphenylethanol; In ethyl acetate; at 20 ℃; for 2h; Reflux; Resolution of racemate;

DOI:10.2174/1570178611666140421231237

upstream raw materials:

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

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

di-tert-butyl dicarbonate

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

Downstream raw materials:

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

saxagliptin

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

(S)-3-hydroxyadamantylglycine-D-cis-4,5-methanoprolinenitrile

Refernces

• 1、 -. "Synthetic method of saxagliptin intermediate". Paragraph 0032; 0041-0043; 0052-0053. . Retrieved 2021/11/21.
• 2、 -. "Intermediates for synthesizing sand Geleg sandbank N-tert-butoxycarbonyl-3-hydroxy-1-adamantyl-D-gly method". Paragraph 0014; 0028; 0029. . Retrieved 2018/02/04.