tert-butyl (S)-(3-(5-(((allyloxy)carbonyl)amino)-4-(2-(hydroxymethyl)pyrrolidine-1-carbonyl)-2-methoxyphenoxy)propyl)carbamate

Base Information

• Chemical Name: tert-butyl (S)-(3-(5-(((allyloxy)carbonyl)amino)-4-(2-(hydroxymethyl)pyrrolidine-1-carbonyl)-2-methoxyphenoxy)propyl)carbamate
• CAS No.: 864672-65-1
• Molecular Formula: C₂₅H₃₇N₃O₈
• Molecular Weight: 507.584
• Mol file: 864672-65-1.mol

Synonyms:tert-butyl (S)-(3-(5-(((allyloxy)carbonyl)amino)-4-(2-(hydroxymethyl)pyrrolidine-1-carbonyl)-2-methoxyphenoxy)propyl)carbamate

Chemical Property of tert-butyl (S)-(3-(5-(((allyloxy)carbonyl)amino)-4-(2-(hydroxymethyl)pyrrolidine-1-carbonyl)-2-methoxyphenoxy)propyl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (S)-(3-(5-(((allyloxy)carbonyl)amino)-4-(2-(hydroxymethyl)pyrrolidine-1-carbonyl)-2-methoxyphenoxy)propyl)carbamate

There total 7 articles about tert-butyl (S)-(3-(5-(((allyloxy)carbonyl)amino)-4-(2-(hydroxymethyl)pyrrolidine-1-carbonyl)-2-methoxyphenoxy)propyl)carbamate 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: 94.0%

tert-butyl (S)-(3-(5-amino-4-(2-(hydroxymethyl)-pyrrolidine-1-carbonyl)-2-methoxyphenoxy)propyl)carbamate (1025740-51-5) + Allyl chloroformate (2937-50-0) → tert-butyl (S)-(3-(5-(((allyloxy)carbonyl)amino)-4-(2-(hydroxymethyl)pyrrolidine-1-carbonyl)-2-methoxyphenoxy)propyl)carbamate (864672-65-1)

Guidance literature:

With pyridine; In dichloromethane; at -10 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acsinfecdis.7b00130

Reference yield:

3-bromopropylamine tert-butylcarbamate (83948-53-2) → tert-butyl (S)-(3-(5-(((allyloxy)carbonyl)amino)-4-(2-(hydroxymethyl)pyrrolidine-1-carbonyl)-2-methoxyphenoxy)propyl)carbamate (864672-65-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 50 °C

2.1: potassium permanganate / acetone; water / Reflux

3.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.33 h

3.2: 15 h / 50 °C

4.1: palladium 10% on activated carbon; hydrogen / ethanol / 2068.65 Torr

5.1: pyridine / dichloromethane / 2 h / -10 - 20 °C / Inert atmosphere

With pyridine; potassium permanganate; palladium 10% on activated carbon; hydrogen; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/acsinfecdis.7b00130

Reference yield:

4-(3-((tert-butoxycarbonyl)amino)propoxy)-5-methoxy-2-nitrobenzoic acid (757189-87-0) → tert-butyl (S)-(3-(5-(((allyloxy)carbonyl)amino)-4-(2-(hydroxymethyl)pyrrolidine-1-carbonyl)-2-methoxyphenoxy)propyl)carbamate (864672-65-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.33 h

1.2: 15 h / 50 °C

2.1: palladium 10% on activated carbon; hydrogen / ethanol / 2068.65 Torr

3.1: pyridine / dichloromethane / 2 h / -10 - 20 °C / Inert atmosphere

With pyridine; palladium 10% on activated carbon; hydrogen; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/acsinfecdis.7b00130

upstream raw materials:

tert-butyl (S)-(3-(5-amino-4-(2-(hydroxymethyl)-pyrrolidine-1-carbonyl)-2-methoxyphenoxy)propyl)carbamate

Allyl chloroformate

3-methoxy-4-(phenylmethoxy)benzaldehyde

3-bromopropylamine tert-butylcarbamate