rac-N-[2-tert-butoxycarbonylamino-2-(3-nitro-phenyl)-propyl]-N-methyl-oxalamic acid ethyl ester

Base Information

• Chemical Name: rac-N-[2-tert-butoxycarbonylamino-2-(3-nitro-phenyl)-propyl]-N-methyl-oxalamic acid ethyl ester
• CAS No.: 1350523-75-9
• Molecular Formula: C₁₉H₂₇N₃O₇
• Molecular Weight: 409.439
• Mol file: 1350523-75-9.mol

Synonyms:rac-N-[2-tert-butoxycarbonylamino-2-(3-nitro-phenyl)-propyl]-N-methyl-oxalamic acid ethyl ester

Chemical Property of rac-N-[2-tert-butoxycarbonylamino-2-(3-nitro-phenyl)-propyl]-N-methyl-oxalamic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of rac-N-[2-tert-butoxycarbonylamino-2-(3-nitro-phenyl)-propyl]-N-methyl-oxalamic acid ethyl ester

There total 8 articles about rac-N-[2-tert-butoxycarbonylamino-2-(3-nitro-phenyl)-propyl]-N-methyl-oxalamic acid ethyl 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: 98.0%

rac-[1-methyl-2-methylamino-1-(3-nitro-phenyl)-ethyl]-carbamic acid tert-butyl ester (1350523-45-3) + Ethyl oxalyl chloride (4755-77-5) → rac-N-[2-tert-butoxycarbonylamino-2-(3-nitro-phenyl)-propyl]-N-methyl-oxalamic acid ethyl ester (1350523-75-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1016/j.bmcl.2011.10.050

Reference yield:

rac-2-amino-2-(3-nitro-phenyl)-propan-1-ol (1270385-54-0) → rac-N-[2-tert-butoxycarbonylamino-2-(3-nitro-phenyl)-propyl]-N-methyl-oxalamic acid ethyl ester (1350523-75-9)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydrogencarbonate / tetrahydrofuran / 0 - 20 °C

2: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C

3: acetic acid / tetrahydrofuran; dichloromethane / 1 h / 20 °C

4: sodium triacetoxy borohydride / 2 h / 20 °C

5: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 °C

With sodium triacetoxy borohydride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmcl.2011.10.050

Reference yield:

rac-2-amino-2-(3-nitro-phenyl)-propionitrile (954272-07-2) → rac-N-[2-tert-butoxycarbonylamino-2-(3-nitro-phenyl)-propyl]-N-methyl-oxalamic acid ethyl ester (1350523-75-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: hydrogenchloride; water / 18 h / Reflux

2.1: thionyl chloride / 0.25 h / 0 °C

2.2: 18 h / Reflux

3.1: sodium tetrahydroborate / ethanol / 3 h / 20 °C

4.1: sodium hydrogencarbonate / tetrahydrofuran / 0 - 20 °C

5.1: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C

6.1: acetic acid / tetrahydrofuran; dichloromethane / 1 h / 20 °C

7.1: sodium triacetoxy borohydride / 2 h / 20 °C

8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 °C

With sodium triacetoxy borohydride; hydrogenchloride; sodium tetrahydroborate; thionyl chloride; water; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1016/j.bmcl.2011.10.050

upstream raw materials:

rac-2-amino-2-(3-nitro-phenyl)-propan-1-ol

rac-[1-methyl-1-(3-nitro-phenyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

rac-[1-methyl-2-methylamino-1-(3-nitro-phenyl)-ethyl]-carbamic acid tert-butyl ester

Ethyl oxalyl chloride

Downstream raw materials:

rac-1,5-dimethyl-5-(3-nitro-phenyl)-piperazine-2,3-dione

rac-3-methoxy-1,5-dimethyl-5-(3-nitro-phenyl)-5,6-dihydro-1H-pyrazin-2-one

rac-3-amino-5-(3-amino-phenyl)-1,5-dimethyl-5,6-dihydro-1H-pyrazin-2-one