Rac-2-[(1R,2R)-2-{[(tert-butoxy)carbonyl]amino}cyclohexyl]acetic acid

Base Information

• Chemical Name: Rac-2-[(1R,2R)-2-{[(tert-butoxy)carbonyl]amino}cyclohexyl]acetic acid
• CAS No.: 143617-91-8
• Molecular Formula: C₁₃H₂₃NO₄
• Molecular Weight: 257.33
• DSSTox Substance ID: DTXSID901148113
• Mol file: 143617-91-8.mol

Synonyms:143617-91-8;Rac-2-[(1R,2R)-2-{[(tert-butoxy)carbonyl]amino}cyclohexyl]acetic acid;rac-2-[(1R,2R)-2-{[(tert-butoxy)carbonyl]amino}cyclohexyl]acetic acid, cis;DTXSID901148113;AKOS034820618;EN300-371653;Z2768165130;Rac-2-[(1R,2R)-2-{[(tert-butoxy)carbonyl]amino}cyclohexyl]aceticacid;rel-(1R,2R)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]cyclohexaneacetic acid;2-[(1R,2R)-2-[(2-Methylpropan-2-yl)oxycarbonylamino]cyclohexyl]acetic acid;1355168-86-3

Chemical Property of Rac-2-[(1R,2R)-2-{[(tert-butoxy)carbonyl]amino}cyclohexyl]acetic acid

Chemical Property:

• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 257.16270821
• Heavy Atom Count: 18
• Complexity: 309

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1CCCCC1CC(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H]1CCCC[C@@H]1CC(=O)O

Technology Process of Rac-2-[(1R,2R)-2-{[(tert-butoxy)carbonyl]amino}cyclohexyl]acetic acid

There total 5 articles about Rac-2-[(1R,2R)-2-{[(tert-butoxy)carbonyl]amino}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: 99.0%

(rac)-trans-octahydro-2-oxo-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester (143617-92-9) → (rac)-trans-2-<<(1,1-dimethylethyl)oxy>carboxamido>cyclohexylacetic acid (143617-91-8,143617-93-0)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; for 2h; Ambient temperature;

DOI:10.1021/jm00099a005

Reference yield: 96.0%

di-tert-butyl dicarbonate (24424-99-5) + (rac)-cis-2-aminocyclohexaneacetic acid (78844-19-6,84673-66-5,84673-67-6,125354-73-6,125354-74-7,143679-78-1) → (rac)-cis-2-<<(1,1-dimethylethoxy)carbonyl>amino>cyclohexaneacetic acid (143617-91-8,143617-93-0)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; for 5h; Ambient temperature;

DOI:10.1021/jm00099a005

Reference yield:

2-(2-nitrophenyl)acetic acid (3740-52-1) → (rac)-cis-2-<<(1,1-dimethylethoxy)carbonyl>amino>cyclohexaneacetic acid (143617-91-8,143617-93-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 49 percent / H₂ / 5 percent Rh/C / ethanol / 6 h / 60 °C / 5171.5 Torr

2: 96 percent / 1 N aq. NaOH / dioxane / 5 h / Ambient temperature

With sodium hydroxide; hydrogen; Rh on carbon; In 1,4-dioxane; ethanol;

DOI:10.1021/jm00099a005

upstream raw materials:

di-tert-butyl dicarbonate

(rac)-cis-2-aminocyclohexaneacetic acid

2-(2-nitrophenyl)acetic acid

(rac)-trans-octahydro-2-oxo-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester