Methyl 4-{[(benzyloxy)carbonyl]amino}-2-oxobutanoate

Base Information

• Chemical Name: Methyl 4-{[(benzyloxy)carbonyl]amino}-2-oxobutanoate
• CAS No.: 81323-56-0
• Molecular Formula: C13H15NO5
• Molecular Weight: 265.266
• DSSTox Substance ID: DTXSID80604080
• Wikidata: Q82501805
• Mol file: 81323-56-0.mol

Synonyms:81323-56-0;SCHEMBL335135;Methyl 4-{[(benzyloxy)carbonyl]amino}-2-oxobutanoate;DTXSID80604080;FMDRKIRRYGEMJF-UHFFFAOYSA-N;4-(benzyloxycarbonylamino)-2-oxobutanoic acid methyl ester

Chemical Property of Methyl 4-{[(benzyloxy)carbonyl]amino}-2-oxobutanoate

Chemical Property:

• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 265.09502258
• Heavy Atom Count: 19
• Complexity: 323

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(=O)CCNC(=O)OCC1=CC=CC=C1

Technology Process of Methyl 4-{[(benzyloxy)carbonyl]amino}-2-oxobutanoate

There total 4 articles about Methyl 4-{[(benzyloxy)carbonyl]amino}-2-oxobutanoate 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:

(4-Bromo-4-methanesulfinyl-3-oxo-butyl)-carbamic acid benzyl ester (81323-55-9) → Methyl N-benzyloxycarbonyl-4-amino-2-oxobutanoate (81323-56-0)

Guidance literature:

With hydrogenchloride; In methanol; at 45 ℃; for 1.5h; Yield given;

DOI:10.1055/s-1982-29691

Reference yield:

3-(benzyloxycarbonylamino)propanoic acid (2304-94-1) → Methyl N-benzyloxycarbonyl-4-amino-2-oxobutanoate (81323-56-0)

Guidance literature:

Multi-step reaction with 2 steps

1: EDCI, DMAP

2: ozone / CH₂Cl₂

With dmap; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;

DOI:10.1016/S0040-4039(99)80114-2

Reference yield:

N-Benzyloxycarbonyl-4-amino-1-methylsulfinyl-2-butanone (54755-78-1) → Methyl N-benzyloxycarbonyl-4-amino-2-oxobutanoate (81323-56-0)

Guidance literature:

Multi-step reaction with 2 steps

1: NBS / acetone / 0.08 h / Ambient temperature

2: aq. HCl / methanol / 1.5 h / 45 °C

With hydrogenchloride; N-Bromosuccinimide; In methanol; acetone;

DOI:10.1055/s-1982-29691

upstream raw materials:

(4-Bromo-4-methanesulfinyl-3-oxo-butyl)-carbamic acid benzyl ester

methanol

3-(benzyloxycarbonylamino)propanoic acid

N-Benzyloxycarbonyl-4-amino-1-methylsulfinyl-2-butanone

Downstream raw materials:

methyl 2-(2-{[(benzyloxy)carbonyl]amino}ethyl)-7-methoxy-3-methyl-6-(1,3-oxazol-5-yl)-4-oxo-1,2,3,4-tetrahydroquinazoline-2-carboxylate

(R)-4-benzyloxycarbonylamino-2-hydroxybutanoic acid

S-4-benzyloxycarbonylamino-2-hydroxybutyric acid