ACS-PNZ-PYRROLIDYL-(BOC)-NSO2NH2

Base Information

• Chemical Name: ACS-PNZ-PYRROLIDYL-(BOC)-NSO2NH2
• CAS No.: 491878-06-9
• Molecular Formula: C₂₀H₂₈N₄O₉S₂
• Molecular Weight: 532.596
• Hs Code.: 2935009090
• Mol file: 491878-06-9.mol

Synonyms:4-Nitrobenzyl(2S,4S)-4-acetylthio-2-[[N-sulfamoyl-N-(tert-butoxycarbonyl)amino]methyl]pyrrolidine-1-carboxylate;

Chemical Property of ACS-PNZ-PYRROLIDYL-(BOC)-NSO2NH2

Chemical Property:

• Appearance/Colour: White or llight yellowish powder
• Melting Point: 124-132 °C
• Refractive Index: 1.616
• Boiling Point: 686.8 °C at 760 mmHg
• PKA: 10.00±0.60(Predicted)
• Flash Point: 369.2 °C
• PSA: 215.81000
• Density: 1.45 g/cm³
• LogP: 4.63680
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

Doripenem side-chain ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ACS-PNZ-PYRROLIDYL-(BOC)-NSO2NH2

There total 10 articles about ACS-PNZ-PYRROLIDYL-(BOC)-NSO2NH2 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: 81.0%

(2S,4S)-4-acetylthio-2-hydroxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (104773-40-2) + N-tert-butoxycarbonylsulfamoyl amine (148017-28-1) → (2S,4S)-4-acetylthio-2-[[N-aminosulfonyl-N-(tert-butyloxycarbonyl)amino]methyl]pyrrolidine-1-carboxylic acid p-nitrobenzyl ester (491878-06-9,571176-82-4)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In ethyl acetate; at 20 ℃; for 2h;

DOI:10.1021/op0340412

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → (2S,4S)-4-acetylthio-2-[[N-aminosulfonyl-N-(tert-butyloxycarbonyl)amino]methyl]pyrrolidine-1-carboxylic acid p-nitrobenzyl ester (491878-06-9,571176-82-4)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium carbonate / toluene; water; methanol / 1 h / 2 - 5 °C

2: triethylamine / toluene / 0.33 h / 20 °C

3: sodium tetrahydroborate / ethyl acetate; methanol / 3 h / 0 - 5 °C

4: toluene; N,N-dimethyl-formamide / 4 h / 65 °C / Large scale

5: di-isopropyl azodicarboxylate; triphenylphosphine / ethyl acetate / 2 h / 20 °C

With sodium tetrahydroborate; di-isopropyl azodicarboxylate; potassium carbonate; triethylamine; triphenylphosphine; In methanol; water; ethyl acetate; N,N-dimethyl-formamide; toluene; 5: |Mitsunobu Displacement;

DOI:10.1021/op0340412

Reference yield:

4R-4-hydroxyproline (51-35-4,30724-02-8) → (2S,4S)-4-acetylthio-2-[[N-aminosulfonyl-N-(tert-butyloxycarbonyl)amino]methyl]pyrrolidine-1-carboxylic acid p-nitrobenzyl ester (491878-06-9,571176-82-4)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium hydroxide / toluene; water / 1 h / 5 °C / Large scale

2: triethylamine / dichloromethane / 0.5 h / 0 °C / Large scale

3: triethylamine / dichloromethane / 0.5 h / -45 °C / Large scale

4: sodium tetrahydroborate / water; dichloromethane; isopropyl alcohol / 0.5 h / -45 °C / Large scale

5: toluene; N,N-dimethyl-formamide / 4 h / 65 °C / Large scale

6: di-isopropyl azodicarboxylate; triphenylphosphine / ethyl acetate / 2 h / 20 °C

With sodium tetrahydroborate; di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine; sodium hydroxide; In dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; toluene; 6: |Mitsunobu Displacement;

DOI:10.1021/op0340412

upstream raw materials:

(2S,4S)-4-acetylthio-2-hydroxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

N-tert-butoxycarbonylsulfamoyl amine

4R-4-hydroxyproline

L-4-hydroxyproline methyl ester hydrochloride

Downstream raw materials:

(4R,5S,6S)-3-[[(3S,5S)-5-[[(aminosulfonyl)amino]methyl]-1-[[(4-nitrophenyl)methoxy]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester

doripenem

Refernces