(2S,4S)-tert-butyl 4-(acetylthio)-2-((tert-butoxycarbonyl(sulfaMoyl)aMino)Methyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: (2S,4S)-tert-butyl 4-(acetylthio)-2-((tert-butoxycarbonyl(sulfaMoyl)aMino)Methyl)pyrrolidine-1-carboxylate
• CAS No.: 148017-43-0
• Molecular Formula: C17H31N3O7S2
• Molecular Weight: 453.581
• Mol file: 148017-43-0.mol

Synonyms:(2S,4S)-(i)-<2-(2,4-dichlorophenyl)-2-<(1H-imidazol-1-yl)methyl>-1,3-dioxolan-4-yl>methyl methanesulfonate;(2S,4S)-1-allyloxycarbonyl-2-(N-sulfamoyl-N-allyloxycarbonylamino)methyl-4-mercaptopyrrolidine;(2S,4S)-1-tert-butoxycarbonyl-4-acetylthio-2-(N-tert-butoxycarbonyl-N-sulfamoylaminomethyl)pyrrolidine;

Chemical Property of (2S,4S)-tert-butyl 4-(acetylthio)-2-((tert-butoxycarbonyl(sulfaMoyl)aMino)Methyl)pyrrolidine-1-carboxylate

Chemical Property:

• Boiling Point: 557.2±60.0 °C(Predicted)
• PKA: 10.00±0.60(Predicted)
• PSA: 169.99000
• Density: 1.31±0.1 g/cm3(Predicted)
• LogP: 3.80370

Purity/Quality:

NLT 98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S,4S)-tert-butyl 4-(acetylthio)-2-((tert-butoxycarbonyl(sulfaMoyl)aMino)Methyl)pyrrolidine-1-carboxylate

There total 5 articles about (2S,4S)-tert-butyl 4-(acetylthio)-2-((tert-butoxycarbonyl(sulfaMoyl)aMino)Methyl)pyrrolidine-1-carboxylate 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) → (2S,4S)-1-tert-butoxycarbonyl-4-acetylthio-2-(N-tert-butoxycarbonyl-N-sulfamoylaminomethyl)pyrrolidine (148017-43-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / NaOH / methanol / 3 h / Ambient temperature

2: 1.) ethyl chloroformate, triethylamine, 2.) sodium borohydride, tetra-n-butylammonium bromide / 1.) CH₂Cl₂, -40 deg C, 40 min, 2.) water, CH₂Cl₂, -10 deg C, 1 h

3: 86 percent / dimethylformamide / 3.75 h / 65 °C

4: triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 4 h / Ambient temperature

With sodium hydroxide; sodium tetrahydroborate; tetrabutylammomium bromide; chloroformic acid ethyl ester; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.7164/antibiotics.49.478

Reference yield:

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid (13726-69-7,946610-68-0) → (2S,4S)-1-tert-butoxycarbonyl-4-acetylthio-2-(N-tert-butoxycarbonyl-N-sulfamoylaminomethyl)pyrrolidine (148017-43-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) ethyl chloroformate, triethylamine, 2.) sodium borohydride, tetra-n-butylammonium bromide / 1.) CH₂Cl₂, -40 deg C, 40 min, 2.) water, CH₂Cl₂, -10 deg C, 1 h

2: 86 percent / dimethylformamide / 3.75 h / 65 °C

3: triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 4 h / Ambient temperature

With sodium tetrahydroborate; tetrabutylammomium bromide; chloroformic acid ethyl ester; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.7164/antibiotics.49.478

Reference yield:

(2S,4R)-N-tetr-butoxycarbonyl-4-methanesulfonyloxy-2-hydroxymethylpyrrolidine (148017-07-6) → (2S,4S)-1-tert-butoxycarbonyl-4-acetylthio-2-(N-tert-butoxycarbonyl-N-sulfamoylaminomethyl)pyrrolidine (148017-43-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / dimethylformamide / 3.75 h / 65 °C

2: triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 4 h / Ambient temperature

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.7164/antibiotics.49.478

upstream raw materials:

N-tert-butoxycarbonylsulfamoyl amine

(2S,4S)-4-acetylthio-1-t-butoxycarbonylpyrrolidine-2-methanol

di-tert-butyl dicarbonate

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Downstream raw materials:

diphenylmethyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[[(3S,5S)-1-(tert-butoxycarbonyl)-5-[N-sulfamoyl-N-(tert-butoxycarbonyl)aminomethyl]pyrrolidin-3-yl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

doripenem

(2S,4S)-1-t-butoxycarbonyl-2-(N-t-butoxycarbonyl-N-sulfamoylamino)methyl-4-mercaptopyrrolidine

Refernces