tert-butyl (S)-(3-(4-(2-(hydroxymethyl)pyrrolidine-carbonyl)-2-methoxy-5-nitrophenoxy)propyl)carbamate

Base Information

• Chemical Name: tert-butyl (S)-(3-(4-(2-(hydroxymethyl)pyrrolidine-carbonyl)-2-methoxy-5-nitrophenoxy)propyl)carbamate
• CAS No.: 864672-64-0
• Molecular Formula: C₂₁H₃₁N₃O₈
• Molecular Weight: 453.492
• Mol file: 864672-64-0.mol

Synonyms:tert-butyl (S)-(3-(4-(2-(hydroxymethyl)pyrrolidine-carbonyl)-2-methoxy-5-nitrophenoxy)propyl)carbamate

Chemical Property of tert-butyl (S)-(3-(4-(2-(hydroxymethyl)pyrrolidine-carbonyl)-2-methoxy-5-nitrophenoxy)propyl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (S)-(3-(4-(2-(hydroxymethyl)pyrrolidine-carbonyl)-2-methoxy-5-nitrophenoxy)propyl)carbamate

There total 5 articles about tert-butyl (S)-(3-(4-(2-(hydroxymethyl)pyrrolidine-carbonyl)-2-methoxy-5-nitrophenoxy)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: 93.0%

pyrrolidine (123-75-1) + methanol (67-56-1) + 4-(3-((tert-butoxycarbonyl)amino)propoxy)-5-methoxy-2-nitrobenzoic acid (757189-87-0) → tert-butyl (S)-(3-(4-(2-(hydroxymethyl)pyrrolidine-carbonyl)-2-methoxy-5-nitrophenoxy)propyl)carbamate (864672-64-0)

Guidance literature:

4-(3-((tert-butoxycarbonyl)amino)propoxy)-5-methoxy-2-nitrobenzoic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); at 30 ℃; for 3h;

pyrrolidine; methanol; In DMF (N,N-dimethyl-formamide); at 20 ℃;

Reference yield: 93.0%

(S)-1-Pyrrolidin-2-yl-methanol (23356-96-9) + 4-(3-((tert-butoxycarbonyl)amino)propoxy)-5-methoxy-2-nitrobenzoic acid (757189-87-0) → tert-butyl (S)-(3-(4-(2-(hydroxymethyl)pyrrolidine-carbonyl)-2-methoxy-5-nitrophenoxy)propyl)carbamate (864672-64-0)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2008.01.096

Reference yield:

vanillin (121-33-5,8014-42-4) → tert-butyl (S)-(3-(4-(2-(hydroxymethyl)pyrrolidine-carbonyl)-2-methoxy-5-nitrophenoxy)propyl)carbamate (864672-64-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: potassium carbonate / acetone / Reflux

2.1: trifluoroacetic acid; potassium nitrate / 0 °C

3.1: water; acetic acid; hydrogen bromide / 1 h / 85 °C

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

5.1: potassium permanganate / acetone; water / Reflux

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

6.2: 15 h / 50 °C

With potassium permanganate; water; hydrogen bromide; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; acetic acid; potassium nitrate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/acsinfecdis.7b00130

upstream raw materials:

(S)-1-Pyrrolidin-2-yl-methanol

4-(3-((tert-butoxycarbonyl)amino)propoxy)-5-methoxy-2-nitrobenzoic acid

pyrrolidine

methanol

Downstream raw materials:

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

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