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

Base Information

• Chemical Name: tert-butyl (S)-(3-(5-amino-4-(2-(hydroxymethyl)-pyrrolidine-1-carbonyl)-2-methoxyphenoxy)propyl)carbamate
• CAS No.: 1025740-51-5
• Molecular Formula: C₂₁H₃₃N₃O₆
• Molecular Weight: 423.51
• Mol file: 1025740-51-5.mol

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

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

There total 5 articles about tert-butyl (S)-(3-(5-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: 100.0%

tert-butyl (S)-(3-(4-(2-(hydroxymethyl)pyrrolidine-carbonyl)-2-methoxy-5-nitrophenoxy)propyl)carbamate (864672-64-0) → tert-butyl (S)-(3-(5-amino-4-(2-(hydroxymethyl)-pyrrolidine-1-carbonyl)-2-methoxyphenoxy)propyl)carbamate (1025740-51-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate;

DOI:10.1016/j.bmcl.2008.01.096

Reference yield:

vanillin (121-33-5,8014-42-4) → tert-butyl (S)-(3-(5-amino-4-(2-(hydroxymethyl)-pyrrolidine-1-carbonyl)-2-methoxyphenoxy)propyl)carbamate (1025740-51-5)

Guidance literature:

Multi-step reaction with 7 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

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

With potassium permanganate; palladium 10% on activated carbon; water; hydrogen bromide; hydrogen; 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 ethanol; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/acsinfecdis.7b00130

Reference yield:

3-methoxy-4-(phenylmethoxy)benzaldehyde (2426-87-1) → tert-butyl (S)-(3-(5-amino-4-(2-(hydroxymethyl)-pyrrolidine-1-carbonyl)-2-methoxyphenoxy)propyl)carbamate (1025740-51-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: trifluoroacetic acid; potassium nitrate / 0 °C

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

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

4.1: potassium permanganate / acetone; water / Reflux

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

5.2: 15 h / 50 °C

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

With potassium permanganate; palladium 10% on activated carbon; water; hydrogen bromide; hydrogen; 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 ethanol; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/acsinfecdis.7b00130

upstream raw materials:

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

3-methoxy-4-(phenylmethoxy)benzaldehyde

vanillin

tert-butyl (3-(4-formyl-2-methoxy-5-nitrophenoxy)-propyl)carbamate

Downstream raw materials:

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