Methyl (2S)-amino(cyclohexyl)acetate hydrochloride

Base Information

• Chemical Name: Methyl (2S)-amino(cyclohexyl)acetate hydrochloride
• CAS No.: 145618-11-7
• Molecular Formula: C9H17NO2
• Molecular Weight: 171.239
• DSSTox Substance ID: DTXSID50443342
• Wikidata: Q76415896
• Mol file: 145618-11-7.mol

Synonyms:145618-11-7;methyl (2S)-2-amino-2-cyclohexylacetate;Methyl (2S)-amino(cyclohexyl)acetate hydrochloride;Methyl (S)-2-amino-2-cyclohexylacetate;Cyclohexaneacetic acid, a-aMino-, Methyl ester, (S)-;SCHEMBL2608454;DTXSID50443342;UUSVVDQFPGXFTQ-QMMMGPOBSA-N;methyl(2s)-amino(cyclohexyl)ethanoate;(s)-amino-cyclohexyl-acetic acid methyl ester;EN300-257658

Chemical Property of Methyl (2S)-amino(cyclohexyl)acetate hydrochloride

Chemical Property:

• Boiling Point: 231.7±13.0 °C(Predicted)
• PKA: 7.65±0.50(Predicted)
• PSA: 52.32000
• Density: 1.033±0.06 g/cm3(Predicted)
• LogP: 1.76730
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 171.125928785
• Heavy Atom Count: 12
• Complexity: 153

Purity/Quality:

98%, 99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(C1CCCCC1)N
• Isomeric SMILES: COC(=O)[C@H](C1CCCCC1)N

Technology Process of Methyl (2S)-amino(cyclohexyl)acetate hydrochloride

There total 29 articles about Methyl (2S)-amino(cyclohexyl)acetate hydrochloride 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%

tert-butyl (S)-(methoxycarbonyl)(cyclohexyl)methylcarbamate (107202-38-0) → (S)-amino(cyclohexyl)acetic acid methyl ester (145618-11-7)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane; for 3h;

DOI:10.1016/j.bmc.2006.10.044

Reference yield: 96.0%

methanol (67-56-1) + (2S)-amino(cyclohexyl)ethanoic acid (14328-51-9) → (S)-amino(cyclohexyl)acetic acid methyl ester (145618-11-7)

Guidance literature:

With sulfuric acid; Reflux;

DOI:10.1016/j.bmcl.2018.03.020

Reference yield:

(R)-Phenylglycine methyl ester (24461-61-8) → (R)-amino(cyclohexyl)acetic acid methyl ester (37763-24-9,145618-11-7)

Guidance literature:

With hydrogen; platinum(IV) oxide; In acetic acid; at 23 ℃; under 760 Torr;

DOI:10.1016/S0040-4039(01)93748-7

upstream raw materials:

methanol

(2S)-amino(cyclohexyl)ethanoic acid

tert-butyl (S)-(methoxycarbonyl)(cyclohexyl)methylcarbamate

N-(tert-butoxycarbonyl)-L-cyclohexylglycine

Downstream raw materials:

(2S)-methyl benzyloxycarbonylaminocyclohexylacetate

methyl (2S)-2-[(2S)-2-{[(tert-butoxy)carbonyl](methyl)amino}propanamido]-2-cyclohexylacetate

(+)-(S)-methyl 2-cyclohexyl-2-(picolinamido)acetate

N-(t-BuO₂CCH₂)-N-Boc-(D)-Chg-OH

Refernces

• 1、 Zhao, Jie,Zhao, Xiao-Jing,Cao, Pei,Liu, Ji-Kai,Wu, Bin. "Polycyclic Azetidines and Pyrrolidines via Palladium-Catalyzed Intramolecular Amination of Unactivated C(sp3)-H Bonds". supporting information. p. 4880 - 4883. Retrieved 2017/09/23.
• 2、 Bach, Peter,Knerr, Laurent,Fjellstr?m, Ola,Hansson, Kenny,Mattsson, Christer,Gustafsson, David. "Design, synthesis, and SAR of a series of activated protein C (APC) inhibitors with selectivity against thrombin for the treatment of haemophilia". . p. 821 - 827. Retrieved 2014/02/14.