Boc-L-cyclohexylglycine

Base Information

• Chemical Name: Boc-L-cyclohexylglycine
• CAS No.: 109183-71-3
• Molecular Formula: C13H23NO4
• Molecular Weight: 257.33
• Hs Code.: 29242990
• European Community (EC) Number: 600-901-4
• DSSTox Substance ID: DTXSID80426481
• Nikkaji Number: J2.376.806B
• Wikidata: Q72449038
• ChEMBL ID: CHEMBL4950952
• Mol file: 109183-71-3.mol

Synonyms:Boc-L-cyclohexylglycine;109183-71-3;Boc-Chg-OH;Boc-L-alpha-cyclohexylglycine;(S)-2-((tert-Butoxycarbonyl)amino)-2-cyclohexylacetic acid;N-Boc-2-Cyclohexyl-L-glycine;boc-l-a-cyclohexylglycine;MFCD00133638;(2S)-2-cyclohexyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid;(2S)-[(tert-butoxycarbonyl)amino](cyclohexyl)acetic acid;(s)-2-(tert-butoxycarbonylamino)-2-cyclohexylacetic acid;(2S)-[(tert-butoxycarbonyl)amino](cyclohexyl)ethanoic acid;(2S)-2-(tert-Butoxycarbonylamino)-2-cyclohexyl-acetic acid;(S)-tert-butoxycarbonylamino-cyclohexyl-acetic acid;(2S)-2-{[(tert-butoxy)carbonyl]amino}-2-cyclohexylacetic acid;boc-cyclohexyl-gly-oh;Boc-Chg-OH,Nonhydrate;Boc-(L)-Chg-OH;n-boc-l-cyclohexylglycine;[(tert-butoxycarbonyl)amino](cyclohexyl)acetic acid;N-Boc-L-2-cyclohexylglycine;SCHEMBL127389;Boc-L-I+/--cyclohexylglycine;CHEMBL4950952;DTXSID80426481;QSUXZIPXYDQFCX-JTQLQIEISA-N;BBL102899;STL556708;AKOS016842309;AC-4302;CS-W002410;DS-1054;HY-W002410;Boc-Chg-OH, >=98.0% (TLC);PD196395;AM20070532;B3839;N-(tert-Butoxycarbonyl)-L-2-cyclohexylglycine;N-(tert-Butoxycarbonyl)-2-cyclohexyl-L-glycine;EN300-1696782;AU-004/43510685;(2s)-tert.butoxycarbonylamino-cyclohexylacetic acid;(S)-tert-butoxycarbonylamino-cyclohexyl acetic acid;J-300445;(2S)-[(tert-butoxycarbonyl)-amino](cyclohexyl)ethanoic acid;(2S)-[(tert-butoxycarbonyl)amino] (cyclohexyl)ethanoic acid

Chemical Property of Boc-L-cyclohexylglycine

Chemical Property:

• Appearance/Colour: 白色粉末
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 83°C(lit.)
• Refractive Index: 1.5
• Boiling Point: 407.9 °C at 760 mmHg
• PKA: 4.01±0.10(Predicted)
• Flash Point: 200.5 °C
• PSA: 75.63000
• Density: 1.111 g/cm³
• LogP: 2.93550
• Storage Temp.: 2-8°C
• Solubility.: soluble in Methanol
• Water Solubility.: Slightly soluble in water.
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 257.16270821
• Heavy Atom Count: 18
• Complexity: 303

Purity/Quality:

98% ^*data from raw suppliers

Boc-L-Cyclohexylglycine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(C1CCCCC1)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](C1CCCCC1)C(=O)O
• Uses: N-Boc-2-cyclohexyl-L-glycine is used as pharmaceutical intermediate. N-Boc-L-cyclohexylglycine has been used as a reactant for the preparation of a potent hepatitis C protease inhibitor.

Technology Process of Boc-L-cyclohexylglycine

There total 12 articles about Boc-L-cyclohexylglycine 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: 98.0%

di-tert-butyl dicarbonate (24424-99-5) + (2S)-amino(cyclohexyl)ethanoic acid (14328-51-9) → N-(tert-butoxycarbonyl)-L-cyclohexylglycine (109183-71-3)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; water; at 20 ℃; for 24h;

DOI:10.1021/acs.jmedchem.7b00514

Reference yield: 86.0%

di-tert-butyl dicarbonate (24424-99-5) → N-(tert-butoxycarbonyl)-L-cyclohexylglycine (109183-71-3)

Guidance literature:

In tetrahydrofuran; sodium hydroxide;

Reference yield: 79.1%

N-(tert-butyloxycarbonyl) azide (1070-19-5) + (2S)-amino(cyclohexyl)ethanoic acid (14328-51-9) → N-(tert-butoxycarbonyl)-L-cyclohexylglycine (109183-71-3)

Guidance literature:

With triethylamine; In water; N,N-dimethyl-formamide; at 40 ℃; for 24h;

DOI:10.1248/cpb.29.1644

upstream raw materials:

N-(tert-butyloxycarbonyl) azide

(2S)-amino(cyclohexyl)ethanoic acid

di-tert-butyl dicarbonate

(S)-1-(cyclohexyl-2-hydroxyethyl)crabamic acid tert-butyl ester

Downstream raw materials:

((S)-1-Cyclohexyl-3-diazo-2-oxo-propyl)-carbamic acid tert-butyl ester

[(2'-tert-butylsulfamoyl-biphenyl-4-ylcarbamoyl)-cyclohexyl-methyl]-carbamic acid tert-butyl ester

methyl (2S,4R)-1-[(2S)-2-cyclohexyl-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxoethyl]-4-[(3-hydroxypropyl)thio]-2-pyrrolidinecarboxylate

methyl (2S,4R)-1-[(2S)-2-cyclohexyl-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxoethyl]-4-[(phenylsulfonyl)amino]-2-pyrrolidinecarboxylate

Refernces

• 1、 -. "SELECTIVE MATRIX METALLOPROTEINASE-13 INHIBITORS". Paragraph 00148. . Retrieved 2019/01/06.
• 2、 Bondada, Lavanya,Rondla, Ramu,Pradere, Ugo,Liu, Peng,Li, Chengwei,Bobeck, Drew,McBrayer, Tamara,Tharnish, Philip,Courcambeck, Jerome,Halfon, Philippe,Whitaker, Tony,Amblard, Franck,Coats, Steven J.,Schinazi, Raymond F.. "Azetidines and spiro azetidines as novel P2 units in hepatitis C virus NS3 protease inhibitors". . p. 6325 - 6330. Retrieved 2013/11/19.