(S) - N- Boc- adamantylglycine

Base Information

• Chemical Name: (S) - N- Boc- adamantylglycine
• CAS No.: 361441-97-6
• Molecular Formula: C17H27NO4
• Molecular Weight: 309.406
• Hs Code.: 2924199090
• Mol file: 361441-97-6.mol

Synonyms:(S) - N- Boc- adamantylglycine

Chemical Property of (S) - N- Boc- adamantylglycine

Chemical Property:

• Melting Point: >300 °C (decomp)(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• Boiling Point: 460.324 °C at 760 mmHg
• PKA: 4.21±0.10(Predicted)
• Flash Point: 232.196 °C
• PSA: 79.12000
• Density: 1.193 g/cm³
• LogP: 3.38510
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-Boc-adamantylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (S)-Boc-adamantylglycine is used to prepare saxagliptin (BMS-477118) as highly potent and long-acting and orally active dipeptidyl peptidase IV inhibitor for treatment of type 2 diabetes.

Technology Process of (S) - N- Boc- adamantylglycine

There total 9 articles about (S) - N- Boc- adamantylglycine 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: 92.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-(+)-(adamant-1-yl)aminoacetic acid hydrochloride (102502-64-7) → (alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid (361441-97-6)

Guidance literature:

With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 20 ℃; for 19h;

Reference yield: 82.0%

C17H27NO3 → (alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid (361441-97-6)

Guidance literature:

With sodium chlorite; potassium dihydrogenphosphate; 2-methyl-but-2-ene; In tert-butyl alcohol; at 0 - 10 ℃; for 19.5h;

DOI:10.1055/s-0030-1258235

Reference yield:

(S)-2-(adamantan-1-yl)-2-(((R)-2-hydroxy-1-phenylethyl)amino)acetonitrile (361441-95-4) → (alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid (361441-97-6)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1021/jm050261p

upstream raw materials:

di-tert-butyl dicarbonate

(S)-(+)-β-amino-1-adamantaneacetic acid

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

1-adamantanemethanol

Downstream raw materials:

(S)-(+)-(adamant-1-yl)aminoacetic acid hydrochloride

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

(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxy-1-adamantyl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

(2S,4S,5R)-2-[(2S)-2-amino-2-(3-hydroxyadamantan-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

Refernces

• 1、 Dong, Jizhe,Gong, Yanchun,Liu, Jun,Chen, Xiangfeng,Wen, Xiaoan,Sun, Hongbin. "Synthesis and biological evaluation of all eight stereoisomers of DPP-IV inhibitor saxagliptin". . p. 1383 - 1393. Retrieved 2014/03/21.
• 2、 Baskakova, Alevtina,Frey, Wolfgang,Jaeger, Volker. "Synthesis of adamantylglycine using a diastereoselective grignard-to-nitrone addition". experimental part. p. 3693 - 3699. Retrieved 2010/12/20.