trans-3-(4-Tert-butoxycarbonylaminocyclohexyl)propionic acid

Base Information

• Chemical Name: trans-3-(4-Tert-butoxycarbonylaminocyclohexyl)propionic acid
• CAS No.: 204245-65-8
• Molecular Formula: C14H25NO4
• Molecular Weight: 271.357
• DSSTox Substance ID: DTXSID60441172
• Mol file: 204245-65-8.mol

Synonyms:204245-65-8;1021853-63-3;TRANS-3-(4-TERT-BUTOXYCARBONYLAMINOCYCLOHEXYL)PROPIONIC ACID;cis-3-(4-tert-Butoxycarbonylaminocyclohexyl)propionic acid;3-[4-[(2-methylpropan-2-yl)oxycarbonylamino]cyclohexyl]propanoic Acid;C14H25NO4;cis-3-(4-tert-Butoxycarbonylaminocyclohexyl)-propionic acid;3-(trans-4-((tert-Butoxycarbonyl)amino)cyclohexyl)propanoic acid;3-{trans-4-[(tert-butoxycarbonyl)amino]cyclohexyl}propanoic acid;trans-3-(4-tert-Butoxycarbonylaminocyclohexyl)-propionic acid;SCHEMBL946942;SCHEMBL946943;SCHEMBL1067922;SCHEMBL12916468;SCHEMBL12946896;DTXSID60441172;WCXYTBUDVLMXND-PHIMTYICSA-N;WCXYTBUDVLMXND-XYPYZODXSA-N;MFCD03844589;MFCD03844590;AKOS027327252;CS-0336526;CS-0339798;A1-00063;A1-00064;cis-3-(4-tert-Butoxycarbonylaminocyclohexyl)propionicacid;trans-3-[4-(Boc-amino)cyclohexyl]propionic acid, 97%;3-(4-{[(tert-butoxy)carbonyl]amino}cyclohexyl)propanoic acid;3-(trans-4-tert-butoxycarbonylamino-cyclohexyl)-propionic acid;3-{cis-4-[(tert-butoxycarbonyl)amino]cyclohexyl}propanoic acid;3-cis-[4-(tert-Butoxycarbonylamino)cyclohexyl]propionic acid;trans-3-[4-(tert-Butoxycarbonylamino)cyclohexyl]propionic acid;3-((1R,4r)-4-((tert-butoxycarbonyl)amino)cyclohexyl)propanoic acid;3-((1r,4r)-4-(tert-butoxycarbonylamino)cyclohexyl)propanoic acid;3-((1S,4s)-4-((tert-butoxycarbonyl)amino)cyclohexyl)propanoic acid;3-{4-[(TERT-BUTOXYCARBONYL)AMINO]CYCLOHEXYL}PROPANOIC ACID;trans-3-(4-((tert-butoxycarbonyl)-amino)cyclohexyl)propionic acid;trans-3-(4-((tert-Butoxycarbonyl)amino)-cyclohexyl)propionic Acid

Chemical Property of trans-3-(4-Tert-butoxycarbonylaminocyclohexyl)propionic acid

Chemical Property:

• PSA: 75.63000
• LogP: 3.32560
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 271.17835828
• Heavy Atom Count: 19
• Complexity: 314

Purity/Quality:

99% ^*data from raw suppliers

trans-3-(4-tert-Butoxycarbonylaminocyclohexyl)-propionic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1CCC(CC1)CCC(=O)O

Technology Process of trans-3-(4-Tert-butoxycarbonylaminocyclohexyl)propionic acid

There total 3 articles about trans-3-(4-Tert-butoxycarbonylaminocyclohexyl)propionic 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: 22.4%

→ 3-(trans-4-(tert-butoxycarbonylamino)cyclohexyl)propanoic acid (204245-65-8)

Guidance literature:

Reference yield:

4-nitro-trans-cinnamic acid (882-06-4) → 3-(trans-4-(tert-butoxycarbonylamino)cyclohexyl)propanoic acid (204245-65-8)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂, aq. NaOH / Ru/C / 17 h / 100 °C / 103430 Torr

2: tetrahydrofuran; H₂O / 16 h / Ambient temperature

With sodium hydroxide; hydrogen; Ru-carbon; In tetrahydrofuran; water;

DOI:10.1021/jm9707378

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + Sodium; 3-(4-amino-cyclohexyl)-propionate → 3-(trans-4-(tert-butoxycarbonylamino)cyclohexyl)propanoic acid (204245-65-8) + 3-{cis-4-[(tert-butoxycarbonyl)amino]cyclohexyl}propanoic acid

Guidance literature:

In tetrahydrofuran; water; for 16h; Ambient temperature;

DOI:10.1021/jm9707378

upstream raw materials:

di-tert-butyl dicarbonate

4-nitro-trans-cinnamic acid

Downstream raw materials:

3-(4-Amino-cyclohexyl)-1-(4-phenyl-piperazin-1-yl)-propan-1-one

{4-[3-Oxo-3-(4-phenyl-piperazin-1-yl)-propyl]-cyclohexyl}-carbamic acid tert-butyl ester

1-(4-Phenyl-piperazin-1-yl)-3-[4-(pyrimidin-2-ylamino)-cyclohexyl]-propan-1-one

{trans-4-[3-hydroxy-2-(3-hydroxy-6-methoxy-quinolin-4-ylmethyl)-propyl]-cyclohexyl}-carbamic acid tert-butyl ester

Refernces

• 1、 Wustrow, David,Belliotti, Thomas,Glase, Shelly,Kesten, Suzanne Ross,Johnson, Don,Colbry, Norman,Rubin, Ronald,Blackburn, Anthony,Akunne, Hyacinth,Corbin, Ann,Duff Davis,Georgic, Lynn,Whetzel, Steven,Zoski, Kim,Heffner, Thomas,Pugsley, Thomas,Wise, Lawrence. "Aminopyrimidines with high affinity for both serotonin and dopamine receptors". . p. 760 - 771. Retrieved 2007/10/03.