(R)-ethyl 4-((tert-butoxycarbonyl)amino)-3-oxopentanoate

Base Information

• Chemical Name: (R)-ethyl 4-((tert-butoxycarbonyl)amino)-3-oxopentanoate
• CAS No.: 69619-22-3
• Molecular Formula: C₁₂H₂₁NO₅
• Molecular Weight: 259.302
• DSSTox Substance ID: DTXSID501165676
• Nikkaji Number: J2.091.290A
• Mol file: 69619-22-3.mol

Synonyms:SCHEMBL15243760;UXXDARYIURDZSU-MRVPVSSYSA-N;DTXSID501165676;69619-22-3;(R)-ethyl 4-((tert-butoxycarbonyl)amino)-3-oxopentanoate;Ethyl (4R)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-oxopentanoate

Chemical Property of (R)-ethyl 4-((tert-butoxycarbonyl)amino)-3-oxopentanoate

Chemical Property:

• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 259.14197277
• Heavy Atom Count: 18
• Complexity: 319

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)CC(=O)C(C)NC(=O)OC(C)(C)C
• Isomeric SMILES: CCOC(=O)CC(=O)[C@@H](C)NC(=O)OC(C)(C)C

Technology Process of (R)-ethyl 4-((tert-butoxycarbonyl)amino)-3-oxopentanoate

There total 3 articles about (R)-ethyl 4-((tert-butoxycarbonyl)amino)-3-oxopentanoate 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: 78.0%

diazoacetic acid ethyl ester (623-73-4) + (2R)-2-N-t-butoxycarbonyl-aminopropanal (82353-56-8) → (R)-ethyl 4-(N-tert-butoxycarbonyl)amino 3-oxopentanoate (69619-22-3,66643-80-9)

Guidance literature:

With tin(ll) chloride; In dichloromethane; at 20 - 25 ℃;

DOI:10.1039/c0ob00199f

Reference yield:

(R)-2-tertbutoxycarbonylamino-1-propanol (79069-13-9,127516-56-7,147252-84-4,106391-86-0) → (R)-ethyl 4-(N-tert-butoxycarbonyl)amino 3-oxopentanoate (69619-22-3,66643-80-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate

2: tin(ll) chloride / dichloromethane / 0.5 h / 20 - 25 °C

With tin(ll) chloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; ethyl acetate;

DOI:10.1039/c1ob05815k

Reference yield:

Boc-(R)-Ala (3744-87-4,7764-95-6,15761-38-3) + Dibasic magnesium salt of ethyl hydrogen malonate (35116-15-5) → (R)-ethyl 4-(N-tert-butoxycarbonyl)amino 3-oxopentanoate (69619-22-3,66643-80-9)

Guidance literature:

Multistep reaction; (i) 1H,1'H-1,1'-sulfinyl-bis-imidazole, (ii) /BRN= 4163159/, (iii) aq. HCl;

upstream raw materials:

Boc-(R)-Ala

Dibasic magnesium salt of ethyl hydrogen malonate

diazoacetic acid ethyl ester

(2R)-2-N-t-butoxycarbonyl-aminopropanal