5(R)-(hydroxymethyl)-3-(3,5-difluoro-4-(1-(benzyloxycarbonyl)-2-(tert-butoxycarbonyl)[1,2,5]triazepan-5-yl)phenyl)oxazolidin-2-one

Base Information

• Chemical Name: 5(R)-(hydroxymethyl)-3-(3,5-difluoro-4-(1-(benzyloxycarbonyl)-2-(tert-butoxycarbonyl)[1,2,5]triazepan-5-yl)phenyl)oxazolidin-2-one
• CAS No.: 952150-39-9
• Molecular Formula: C₂₇H₃₂F₂N₄O₇
• Molecular Weight: 562.57
• Mol file: 952150-39-9.mol

Synonyms:5(R)-(hydroxymethyl)-3-(3,5-difluoro-4-(1-(benzyloxycarbonyl)-2-(tert-butoxycarbonyl)[1,2,5]triazepan-5-yl)phenyl)oxazolidin-2-one

Chemical Property of 5(R)-(hydroxymethyl)-3-(3,5-difluoro-4-(1-(benzyloxycarbonyl)-2-(tert-butoxycarbonyl)[1,2,5]triazepan-5-yl)phenyl)oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5(R)-(hydroxymethyl)-3-(3,5-difluoro-4-(1-(benzyloxycarbonyl)-2-(tert-butoxycarbonyl)[1,2,5]triazepan-5-yl)phenyl)oxazolidin-2-one

There total 5 articles about 5(R)-(hydroxymethyl)-3-(3,5-difluoro-4-(1-(benzyloxycarbonyl)-2-(tert-butoxycarbonyl)[1,2,5]triazepan-5-yl)phenyl)oxazolidin-2-one 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%

5-(4-benzyloxycarbonylamino-2,6-difluorophenyl)[1,2,5]triazepane-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester (952150-38-8) + (R)-glycidyl butyrate (60456-26-0) → 5(R)-(hydroxymethyl)-3-(3,5-difluoro-4-(1-(benzyloxycarbonyl)-2-(tert-butoxycarbonyl)[1,2,5]triazepan-5-yl)phenyl)oxazolidin-2-one (952150-39-9)

Guidance literature:

5-(4-benzyloxycarbonylamino-2,6-difluorophenyl)[1,2,5]triazepane-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.0833333h;

(R)-glycidyl butyrate; In tetrahydrofuran; hexane; at 20 ℃; for 0.333333h;

With potassium carbonate; In methanol; at 20 ℃; for 1h;

Reference yield:

3,4,5-trifluoronitrobenzene (66684-58-0) → 5(R)-(hydroxymethyl)-3-(3,5-difluoro-4-(1-(benzyloxycarbonyl)-2-(tert-butoxycarbonyl)[1,2,5]triazepan-5-yl)phenyl)oxazolidin-2-one (952150-39-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / Reflux

2.1: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C / 760.05 Torr

3.1: sodium carbonate / methanol / 0.5 h

4.1: n-butyllithium / hexane; tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

4.2: 23.17 h / -78 - 20 °C / Inert atmosphere

With n-butyllithium; palladium 10% on activated carbon; hydrogen; sodium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; acetonitrile;

DOI:10.1016/j.ejmech.2013.03.003

Reference yield:

5-(2,6-difluoro-4-nitrophenyl)[1,2,5]triazepane-1-carboxylic acid tert-butyl ester (1443005-31-9) → 5(R)-(hydroxymethyl)-3-(3,5-difluoro-4-(1-(benzyloxycarbonyl)-2-(tert-butoxycarbonyl)[1,2,5]triazepan-5-yl)phenyl)oxazolidin-2-one (952150-39-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C / 760.05 Torr

2.1: sodium carbonate / methanol / 0.5 h

3.1: n-butyllithium / hexane; tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

3.2: 23.17 h / -78 - 20 °C / Inert atmosphere

With n-butyllithium; palladium 10% on activated carbon; hydrogen; sodium carbonate; In tetrahydrofuran; methanol; hexane;

DOI:10.1016/j.ejmech.2013.03.003

upstream raw materials:

5-(4-benzyloxycarbonylamino-2,6-difluorophenyl)[1,2,5]triazepane-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

(R)-glycidyl butyrate

3,4,5-trifluoronitrobenzene

5-(2,6-difluoro-4-nitrophenyl)[1,2,5]triazepane-1-carboxylic acid tert-butyl ester

Downstream raw materials:

5(R)-(isoxazol-3-yl-N-(tert-butoxycarbonyl)aminomethyl)-3-(3,5-difluoro-4-(1-(benzyloxycarbonyl)-2-(tert-butoxycarbonyl)[1,2,5]triazepan-5-yl)phenyl)oxazolidin-2-one