Methyl (alphaR)-alpha-[[2-(1,1-dimethylethoxy)-2-oxoethyl]amino]cyclohexanepropanoate

Base Information

• Chemical Name: Methyl (alphaR)-alpha-[[2-(1,1-dimethylethoxy)-2-oxoethyl]amino]cyclohexanepropanoate
• CAS No.: 190904-17-7
• Molecular Formula: C₁₆H₂₉NO₄
• Molecular Weight: 299.411
• DSSTox Substance ID: DTXSID101140046
• Mol file: 190904-17-7.mol

Synonyms:DTXSID101140046;Methyl (alphaR)-alpha-[[2-(1,1-dimethylethoxy)-2-oxoethyl]amino]cyclohexanepropanoate;190904-17-7

Chemical Property of Methyl (alphaR)-alpha-[[2-(1,1-dimethylethoxy)-2-oxoethyl]amino]cyclohexanepropanoate

Chemical Property:

• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 299.20965841
• Heavy Atom Count: 21
• Complexity: 343

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CNC(CC1CCCCC1)C(=O)OC
• Isomeric SMILES: CC(C)(C)OC(=O)CN[C@H](CC1CCCCC1)C(=O)OC

Technology Process of Methyl (alphaR)-alpha-[[2-(1,1-dimethylethoxy)-2-oxoethyl]amino]cyclohexanepropanoate

There total 6 articles about Methyl (alphaR)-alpha-[[2-(1,1-dimethylethoxy)-2-oxoethyl]amino]cyclohexanepropanoate 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: 80.0%

bromoacetic acid tert-butyl ester (5292-43-3) + (R)-2-Amino-3-cyclohexyl-propionic acid methyl ester (769891-92-1,789460-77-1) → N-(tert-butyloxycarbonylmethyl)-D-Cha-OMe (190904-17-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 50 ℃;

DOI:10.1016/S0960-894X(98)00650-7

Reference yield: 58.0%

bromoacetic acid tert-butyl ester (5292-43-3) + methyl (R)-2-amino-3-cyclohexylpropanoate hydrochloride (144644-00-8) → N-(tert-butyloxycarbonylmethyl)-D-Cha-OMe (190904-17-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; at 20 ℃; for 36h; pH=9;

DOI:10.1016/j.bmcl.2013.12.094

Reference yield:

3-cyclohexyl-D-alanine (58717-02-5) → N-(tert-butyloxycarbonylmethyl)-D-Cha-OMe (190904-17-7)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / 18 h / -20 °C / Reflux

2: N-ethyl-N,N-diisopropylamine / 36 h / 20 °C / pH 9

With thionyl chloride; N-ethyl-N,N-diisopropylamine;

DOI:10.1016/j.bmcl.2013.12.094

upstream raw materials:

bromoacetic acid tert-butyl ester

(R)-2-Amino-3-cyclohexyl-propionic acid methyl ester

methyl (R)-2-amino-3-cyclohexylpropanoate hydrochloride

D-cyclohexylalanine hydrochloride

Downstream raw materials:

N-(tert-butyloxycarbonylmethyl)-N-Boc-D-Cha-OMe

(2R)-2-[(tert-butoxycarbonyl)(2-tert-butoxy-2-oxoethyl)amino]-3-cyclohexylpropanoic acid

{[(R)-2-(tert-Butoxycarbonyl-tert-butoxycarbonylmethyl-amino)-3-cyclohexyl-propionyl]-cyclopentyl-amino}-acetic acid

1-[2-(tert-butoxycarbonyl-tert-butoxycarbonylmethyl-amino)-3-cyclohexyl-propionyl]-2,5-dihydro-1H-pyrrole-2-carboxylic acid