(1-{[(Tert-butoxycarbonyl)amino]methyl}cyclohexyl)acetic acid

Base Information

• Chemical Name: (1-{[(Tert-butoxycarbonyl)amino]methyl}cyclohexyl)acetic acid
• CAS No.: 227626-60-0
• Molecular Formula: C14H25 N O4
• Molecular Weight: 271.357
• Hs Code.: 29225090
• European Community (EC) Number: 864-755-5
• DSSTox Substance ID: DTXSID70373152
• Wikidata: Q82161328
• Mol file: 227626-60-0.mol

Synonyms:227626-60-0;2-(1-(((tert-Butoxycarbonyl)amino)methyl)cyclohexyl)acetic acid;(1-{[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)acetic acid;[1-(n-boc-aminomethyl)-cyclohexyl]-acetic acid;[1-(Tert-Butoxycarbonylamino-Methyl)-Cyclohexyl]-Acetic Acid;2-[1-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]cyclohexyl]acetic Acid;[1-(N-Boc-aminomethyl)cyclohexyl]acetic acid;MFCD03839829;(1-{[(tert-Butoxycarbonyl)amino]methyl}-cyclohexyl)acetic acid;2-[1-[(Boc-amino)methyl]cyclohexyl]acetic acid;boc-gabapentin;(1-(((tert-butoxycarbonyl)amino)methyl)cyclohexyl)acetic acid;N-rt-Butyloxycarbonyl Gabapentin;SCHEMBL1076767;DTXSID70373152;YOOHANJKYCQHED-UHFFFAOYSA-N;BBL010437;STK716517;AKOS005175128;BS-11768;SY064308;2-n-boc-aminomethyl-2-cyclohexylacetic acid;CS-0154395;FT-0684281;[1-(N-Boc-aminomethyl)-cyclohexyl]-aceticacid;EN300-137107;Z839048550;1-(N-tert-butoxycarbonylaminomethyl) cyclohexan acetic acid;1-(n-tert-butoxycarbonylaminomethyl)cyclohexan acetic acid;1-(tert-butoxycarbonylamino-methyl)-cyclohexyl-acetic acid;1-[(tert-Butoxycarbonyl)aminomethyl]-1-Cyclohexane Acetic Acid;2-(1-(((tert-Butoxycarbonyl)amino)methyl)cyclohexyl)aceticacid;2-(1-((tert-butoxycarbonylamino)methyl)cyclohexyl)ethanoic acid;2-[1-({[(tert-butoxy)carbonyl]amino}methyl)cyclohexyl]acetic acid;[1-(tert-Butoxycarbonylamino-methyl)-cyclohexyl]-acetic acid, AldrichCPR;3-(tert-butoxycarbonyl)-2-cyclohexylpropanoic acid;[1-(N-BOC-AMINOMETHYL)-CYCLOHEXYL]-ACETIC ACID

Chemical Property of (1-{[(Tert-butoxycarbonyl)amino]methyl}cyclohexyl)acetic acid

Chemical Property:

• Vapor Pressure: 2.45E-08mmHg at 25°C
• Melting Point: 127-128 °C
• Boiling Point: 422.9°Cat760mmHg
• PKA: 4.72±0.10(Predicted)
• Flash Point: 209.6°C
• PSA: 75.63000
• Density: 1.072g/cm³
• LogP: 3.32720
• Storage Temp.: 2-8°C
• Solubility.: Dichloromethane
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 271.17835828
• Heavy Atom Count: 19
• Complexity: 327

Purity/Quality:

98%min ^*data from raw suppliers

N-rt-Butyloxycarbonyl Gabapentin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCC1(CCCCC1)CC(=O)O
• Uses: Protected Gabapentin (G117250). Amino acid structurally related to γ-Aminobutyric Acid (GABA), designed to cross the blood brain barrier. Used as an anticonvulsant.

Technology Process of (1-{[(Tert-butoxycarbonyl)amino]methyl}cyclohexyl)acetic acid

There total 6 articles about (1-{[(Tert-butoxycarbonyl)amino]methyl}cyclohexyl)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%

di-tert-butyl dicarbonate (24424-99-5) + H-Gpn-OH (60142-96-3) → N-Boc-gabapentin (227626-60-0)

Guidance literature:

In tetrahydrofuran; water; at 0 - 20 ℃; Schlenk technique; Inert atmosphere;

DOI:10.1002/anie.201912907

Reference yield: 95.0%

di-tert-butyl dicarbonate (24424-99-5) + 1-(aminomethyl)cyclohexaneacetic acid hydrochloride → N-Boc-gabapentin (227626-60-0)

Guidance literature:

1-(aminomethyl)cyclohexaneacetic acid hydrochloride; With sodium hydroxide; In 1,4-dioxane; water; for 0.25h; pH=> 8; Cooling with ice;

di-tert-butyl dicarbonate; In 1,4-dioxane; water; at 20 ℃;

DOI:10.1039/c6ob00380j

Reference yield: 84.0%

3-oxo-2-aza-spiro[4.5]decane-2-carboxylic acid tert-butyl ester (898552-75-5) → N-Boc-gabapentin (227626-60-0)

Guidance literature:

3-oxo-2-aza-spiro[4.5]decane-2-carboxylic acid tert-butyl ester; With lithium hydroxide; water; In tetrahydrofuran; at 25 ℃; for 6h;

With hydrogenchloride; In water; pH=3;

upstream raw materials:

3-oxo-2-aza-spiro[4.5]decane-2-carboxylic acid tert-butyl ester

di-tert-butyl dicarbonate

H-Gpn-OH

gabapentin-lactam

Downstream raw materials:

[1-(tert-butoxycarbonylamino-methyl)-cyclohexyl]-acetic acid 2-hydroxy-propyl ester

[1-(tert-butoxycarbonylamino-methyl)-cyclohexyl]-acetic acid 4-hydroxy-butyl ester

[1-(tert-butoxycarbonylamino-methyl)-cyclohexyl]-acetic acid 6-hydroxy-hexyl ester

[1-(tert-butoxycarbonylamino-methyl)-cyclohexyl]-acetic acid 3-hydroxy-propyl ester

Refernces

• 1、 Bellotti, Peter,Glorius, Frank,Patra, Tuhin,Strieth-Kalthoff, Felix. "Photosensitized Intermolecular Carboimination of Alkenes through the Persistent Radical Effect". supporting information. p. 3172 - 3177. Retrieved 2020/02/05.
• 2、 Tahir, Saba,Mahmood, Tariq,Dastgir, Faiqa,Haq, Ihsan-ul,Waseem, Amir,Rashid, Umer. "Design, synthesis and anti-bacterial studies of piperazine derivatives against drug resistant bacteria". supporting information. p. 224 - 231. Retrieved 2019/02/05.