2-((tert-Butoxycarbonyl)amino)-3-methoxy-3-oxopropanoic acid

Base Information

• Chemical Name: 2-((tert-Butoxycarbonyl)amino)-3-methoxy-3-oxopropanoic acid
• CAS No.: 61172-71-2
• Molecular Formula: C9H15NO6
• Molecular Weight: 233.221
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID40456244
• Mol file: 61172-71-2.mol

Synonyms:61172-71-2;2-((tert-Butoxycarbonyl)amino)-3-methoxy-3-oxopropanoic acid;2-(tert-butoxycarbonylamino)-3-methoxy-3-oxopropanoic acid;3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropanoic acid;BOC-NHCH(CO2Me)CO2H;DTXSID40456244;IWNBSNGOUCJPKH-UHFFFAOYSA-N;2-((tert-Butoxycarbonyl)amino)-3-methoxy-3-oxopropanoicacid;AKOS016000735;Methyl N-(tert-butoxycarbonyl)-3-oxoserinate;2-tert-butoxycarbonylaminomalonic acid monomethyl ester;2-{[(tert-butoxy)carbonyl]amino}-3-methoxy-3-oxopropanoic acid

Chemical Property of 2-((tert-Butoxycarbonyl)amino)-3-methoxy-3-oxopropanoic acid

Chemical Property:

• PSA: 105.42000
• LogP: 0.34170
• Storage Temp.: 2-8°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 233.08993720
• Heavy Atom Count: 16
• Complexity: 293

Purity/Quality:

≥99.0% ^*data from raw suppliers

2-((tert-Butoxycarbonyl)amino)-3-methoxy-3-oxopropanoicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(C(=O)O)C(=O)OC

Technology Process of 2-((tert-Butoxycarbonyl)amino)-3-methoxy-3-oxopropanoic acid

There total 6 articles about 2-((tert-Butoxycarbonyl)amino)-3-methoxy-3-oxopropanoic 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: 91.0%

dimethyl 2-(tert-butoxycarbonylamino)malonate (61172-70-1) → 2-(tert-butoxycarbonylamino)-3-methoxy-3-oxopropanoic acid (61172-71-2)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; for 15h; Ambient temperature;

DOI:10.1055/s-1992-26351

Reference yield:

N-(tert-butoxycarbonyl)glycine methyl ester (31954-27-5) + carbon dioxide (124-38-9,18923-20-1) → 2-(tert-butoxycarbonylamino)-3-methoxy-3-oxopropanoic acid (61172-71-2)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; lithium diisopropyl amide; Yield given. Multistep reaction; 1.) THF, -75 deg C;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 2-(tert-butoxycarbonylamino)-3-methoxy-3-oxopropanoic acid (61172-71-2)

Guidance literature:

Multi-step reaction with 2 steps

1: KHCO₃ / H₂O; tetrahydrofuran; dioxane / 1.) 0 deg C, 2 h, 2.) room temperature

2: KOH / ethanol / 0 °C

With potassium hydroxide; potassium hydrogencarbonate; In tetrahydrofuran; 1,4-dioxane; ethanol; water;

DOI:10.1016/S0040-4020(99)00084-8

upstream raw materials:

N-(tert-butoxycarbonyl)glycine methyl ester

carbon dioxide

dimethyl 2-(tert-butoxycarbonylamino)malonate

BOC-glycine

Downstream raw materials:

4,4'-dibenzyloxy-3-<(R,S)-2-(tert-butoxycarbonylamino)-2-methoxycarbonyl-1-oxoethyl>-3'-(1,3-dioxan-2-yl)biphenyl

2-tert-butoxycarbonylamino-N-[1-tert-butoxycarbonyl-2-(4-hydroxy-phenyl)-ethyl]-malonamic acid methyl ester

2-tert-butoxycarbonylamino-N-(1-tert-butoxycarbonyl-2-phenyl-ethyl)-malonamic acid methyl ester

N-[2-(4-benzyloxy-phenyl)-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-2-tert-butoxycarbonylamino-malonamic acid methyl ester

Refernces

• 1、 Matt, Thomas,Seebach, Dieter. "C-Alkylation of Peptides Containing Aminomalonate and (Amino)(cyano)acetate Residues". . p. 1845 - 1895. Retrieved 2007/10/03.
• 2、 Schmidt,Leitenberger,Griesser,Schmidt,Meyer. "Total synthesis of the biphenomycins; V. Synthesis of biphenomycin A". . p. 1248 - 1254. Retrieved 2007/10/02.