4-(N-Boc-amino)-3-oxo-pentanoic Acid Methyl Ester

Base Information

• Chemical Name: 4-(N-Boc-amino)-3-oxo-pentanoic Acid Methyl Ester
• CAS No.: 101669-78-7
• Molecular Formula: C₁₁H₁₉NO₅
• Molecular Weight: 245.276
• DSSTox Substance ID: DTXSID40460225
• Mol file: 101669-78-7.mol

Synonyms:4-(N-Boc-amino)-3-oxo-pentanoic Acid Methyl Ester;101669-78-7;methyl 4-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopentanoate;SCHEMBL15228565;DTXSID40460225;AKOS030255440;FT-0663457;J-000469;METHYL 4-[(TERT-BUTOXYCARBONYL)AMINO]-3-OXOPENTANOATE

Chemical Property of 4-(N-Boc-amino)-3-oxo-pentanoic Acid Methyl Ester

Chemical Property:

• Melting Point: 45-48°C
• PSA: 81.70000
• LogP: 1.42270
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Methasnol
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 245.12632271
• Heavy Atom Count: 17
• Complexity: 306

Purity/Quality:

95% ^*data from raw suppliers

4-(N-Boc-amino)-3-oxo-pentanoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 4-(N-Boc-amino)-3-oxo-pentanoic Acid Methyl Ester

There total 6 articles about 4-(N-Boc-amino)-3-oxo-pentanoic Acid Methyl Ester 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:

L-N-Boc-Ala (15761-38-3) + monomethyl monopotassium malonate (38330-80-2) → methyl (S)-4-[(tert-butoxycarbonyl)amino]-3-oxopentanoate (101669-78-7) + methyl (R)-4-[(tert-butoxycarbonyl)amino]-3-oxopentanoate (119960-02-0)

Guidance literature:

L-N-Boc-Ala; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

monomethyl monopotassium malonate; With magnesium chloride; In tetrahydrofuran; at 20 ℃; for 24h; Overall yield = 91 %; Overall yield = 2.23 g; Inert atmosphere;

DOI:10.1016/j.tet.2013.11.008

Reference yield:

L-N-Boc-Ala (15761-38-3) → methyl (S)-4-[(tert-butoxycarbonyl)amino]-3-oxopentanoate (101669-78-7)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 0.5 h / Ambient temperature

2: MgCl₂ / tetrahydrofuran / 50 °C

With magnesium chloride; In tetrahydrofuran;

DOI:10.1006/bioo.1998.1094

Reference yield:

L-N-Boc-Ala (15761-38-3) → methyl (S)-4-[(tert-butoxycarbonyl)amino]-3-oxopentanoate (101669-78-7)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 2 h / 20 °C

2: MgCl₂ / tetrahydrofuran / 7 h / 20 - 45 °C / other N-protected aminoacylimidazoles; other reagents

With magnesium chloride; In tetrahydrofuran;

upstream raw materials:

L-N-Boc-Ala

[(1S)-2-imidazol-1-yl-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester

monomethyl monopotassium malonate

Downstream raw materials:

(4S,5R)-5-[(R)-2-Benzyloxycarbonylamino-3-(N'-benzyloxycarbonylmethyl-N'-methyl-hydrazinocarbonyl)-propyl]-2,2,4-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(3R,5R,6S)-3-Benzyloxycarbonylamino-6-tert-butoxycarbonylamino-5-hydroxy-heptanoic acid methyl ester

(4R,6R)-4-benzyloxycarbonylamino-6-<(1S)-1-(tert-butoxycarbonylamino)ethyl>tetrahydropyran-2-one

[(R)-2-((S)-1-tert-Butoxycarbonylamino-ethyl)-6-oxo-tetrahydro-pyran-4-yl]-carbamic acid benzyl ester

Refernces

• 1、 Gro?elj, Uro?,?or?, Mojca,Golobi?, Amalija,Stanovnik, Branko,Svete, Jurij. "α-Amino acid derived enaminones and their application in the synthesis of N-protected methyl 5-substituted-4-hydroxypyrrole-3-carboxylates and other heterocycles". . p. 11092 - 11108. Retrieved 2014/01/06.
• 2、 Hashiguchi, Shohei,Kawada, Akira,Natsugari, Hideaki. "Stereoselective Synthesis of Sperabillins and Related Compounds". . p. 2435 - 2444. Retrieved 2007/10/02.