benzyl (2S)-1-{[(2R)-2-methyl-7-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl]carbonyl}-2-pyrrolidinecarboxylate

Base Information

• Chemical Name: benzyl (2S)-1-{[(2R)-2-methyl-7-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl]carbonyl}-2-pyrrolidinecarboxylate
• CAS No.: 727993-98-8
• Molecular Formula: C₂₂H₂₁N₃O₇
• Molecular Weight: 439.425
• Mol file: 727993-98-8.mol

Synonyms:benzyl (2S)-1-{[(2R)-2-methyl-7-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl]carbonyl}-2-pyrrolidinecarboxylate

Chemical Property of benzyl (2S)-1-{[(2R)-2-methyl-7-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl]carbonyl}-2-pyrrolidinecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2S)-1-{[(2R)-2-methyl-7-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl]carbonyl}-2-pyrrolidinecarboxylate

There total 3 articles about benzyl (2S)-1-{[(2R)-2-methyl-7-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl]carbonyl}-2-pyrrolidinecarboxylate 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: 20.0%

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride (16652-71-4) + 3,4-dihydro-2-methyl-7-nitro-3-oxo-2H-1,4-benzoxazine-2-carboxylic acid (154365-43-2) → benzyl (2S)-1-{[(2R)-2-methyl-7-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl]carbonyl}-2-pyrrolidinecarboxylate (727993-98-8) + benzyl (2S)-1-{[(2S)-2-methyl-7-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl]carbonyl}-2-pyrrolidinecarboxylate (727994-28-7)

Guidance literature:

With diphenyl-phosphinic acid; triethylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 61h;

DOI:10.1039/b400490f

Reference yield:

3,4-dihydro-2-methyl-7-nitro-3-oxo-2H-1,4-benzoxazine-2-carboxylic acid ethyl ester (154365-36-3) → benzyl (2S)-1-{[(2R)-2-methyl-7-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl]carbonyl}-2-pyrrolidinecarboxylate (727993-98-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / aq. LiOH / methanol / 12 h

2: 19 percent / DPPA; Et₃N / dimethylformamide / 61 h / 0 - 20 °C

With lithium hydroxide; diphenyl-phosphinic acid; triethylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.1039/b400490f

Reference yield:

5-Nitro-2-aminophenol (121-88-0) → benzyl (2S)-1-{[(2R)-2-methyl-7-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl]carbonyl}-2-pyrrolidinecarboxylate (727993-98-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: KF / dimethylformamide / 0.25 h / 20 °C

1.2: 75 percent / dimethylformamide / 6 h / 60 °C

2.1: 97 percent / aq. LiOH / methanol / 12 h

3.1: 19 percent / DPPA; Et₃N / dimethylformamide / 61 h / 0 - 20 °C

With potassium fluoride; lithium hydroxide; diphenyl-phosphinic acid; triethylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.1039/b400490f

upstream raw materials:

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride

3,4-dihydro-2-methyl-7-nitro-3-oxo-2H-1,4-benzoxazine-2-carboxylic acid

3,4-dihydro-2-methyl-7-nitro-3-oxo-2H-1,4-benzoxazine-2-carboxylic acid ethyl ester

5-Nitro-2-aminophenol