1-Pyrrolidinecarboxylic acid, 3-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-4-(methoxyimino)-, 1,1-dimethylethyl ester, (4Z)-

Base Information

• Chemical Name: 1-Pyrrolidinecarboxylic acid, 3-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-4-(methoxyimino)-, 1,1-dimethylethyl ester, (4Z)-
• CAS No.: 197143-34-3
• Molecular Formula: C16H29N3O5
• Molecular Weight: 343.423
• DSSTox Substance ID: DTXSID701107715
• Mol file: 197143-34-3.mol

Synonyms:197143-34-3;1-Pyrrolidinecarboxylic acid, 3-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-4-(methoxyimino)-, 1,1-dimethylethyl ester, (4Z)-;SCHEMBL14493183;DTXSID701107715;1,1-Dimethylethyl (4Z)-3-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-4-(methoxyimino)-1-pyrrolidinecarboxylate;tert-butyl (3Z)-3-methoxyimino-4-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidine-1-carboxylate

Chemical Property of 1-Pyrrolidinecarboxylic acid, 3-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-4-(methoxyimino)-, 1,1-dimethylethyl ester, (4Z)-

Chemical Property:

• PSA: 89.46000
• LogP: 2.70920
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 343.21072103
• Heavy Atom Count: 24
• Complexity: 491

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCC1CN(CC1=NOC)C(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)(C)OC(=O)NCC\1CN(C/C1=N\OC)C(=O)OC(C)(C)C

Technology Process of 1-Pyrrolidinecarboxylic acid, 3-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-4-(methoxyimino)-, 1,1-dimethylethyl ester, (4Z)-

There total 1 articles about 1-Pyrrolidinecarboxylic acid, 3-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-4-(methoxyimino)-, 1,1-dimethylethyl ester, (4Z)- 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:

di-tert-butyl dicarbonate (24424-99-5) + 4-cyano-3-methoxyimino-1-(N-tert-butoxycarbonyl)pyrrolidine (782479-64-5) → 4-cyano-3-amino-1-(N-tert-butoxycarbonyl)-3,4-pyrroline (1227461-24-6) + 4-aminomethyl-3-Z-methoxyimino-1-(N-tert-butoxycarbonyl)pyrrolidine + 4-(N-tert-butoxycarbonyl)aminomethyl-3-Z-methoxyimino-1-(N-tert-butoxycarbonyl)pyrrolidine (197143-34-3)

Guidance literature:

With 1% Pd on activated carbon; hydrogen; In water; isopropyl alcohol; at 24.84 ℃; for 7h; under 25858.1 Torr; Reagent/catalyst; Pressure; Temperature;

DOI:10.1021/op049913u

Reference yield:

4-(N-tert-butoxycarbonyl)aminomethyl-3-Z-methoxyimino-1-(N-tert-butoxycarbonyl)pyrrolidine (197143-34-3) → gemifloxacin (175463-14-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / AcCl, MeOH / 0.83 h / Ambient temperature

2: 85 percent / DBU / acetonitrile / 0.5 h / Ambient temperature

With methanol; 1,8-diazabicyclo[5.4.0]undec-7-ene; acetyl chloride; In acetonitrile;

DOI:10.1021/jm970202e

Reference yield:

4-(N-tert-butoxycarbonyl)aminomethyl-3-Z-methoxyimino-1-(N-tert-butoxycarbonyl)pyrrolidine (197143-34-3) → 7-(4-aminomethyl-3-methoxyiminopyrrolidin-1-yl)-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / AcCl, MeOH / 0.83 h / Ambient temperature

2: 25 percent / DBU / acetonitrile / 0.5 h / Ambient temperature

With methanol; 1,8-diazabicyclo[5.4.0]undec-7-ene; acetyl chloride; In acetonitrile;

DOI:10.1021/jm970202e

upstream raw materials:

di-tert-butyl dicarbonate

4-cyano-3-methoxyimino-1-(N-tert-butoxycarbonyl)pyrrolidine

Downstream raw materials:

gemifloxacin