(3S,5R)-5-amino-N-(1-isobutyl-3-methylbutyl)-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxamide

Base Information

Chemical Name:(3S,5R)-5-amino-N-(1-isobutyl-3-methylbutyl)-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxamide
CAS No.:1448902-66-6
Molecular Formula:C₂₁H₃₄N₄O₅S
Molecular Weight:454.591
Hs Code.:

Synonyms:(3S,5R)-5-amino-N-(1-isobutyl-3-methylbutyl)-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxamide

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Chemical Property of (3S,5R)-5-amino-N-(1-isobutyl-3-methylbutyl)-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxamide

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Technology Process of (3S,5R)-5-amino-N-(1-isobutyl-3-methylbutyl)-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxamide

There total 6 articles about (3S,5R)-5-amino-N-(1-isobutyl-3-methylbutyl)-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxamide 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: 76.0%

: 1448902-65-5
2-trimethylsilylethyl N-{(3R,5S)-5-[(1-isobutyl-3-methylbutyl)carbamoyl]-1-(2-nitrophenyl)sulfonyl-3-piperidyl}carbamate

: 1448902-66-6
(3S,5R)-5-amino-N-(1-isobutyl-3-methylbutyl)-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxamide

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50 ℃; for 3h;
DOI:10.1016/j.bmc.2013.06.057

Reference yield:

: (3S,5R)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)piperidine-3-carboxylic acid

: 1448902-66-6
(3S,5R)-5-amino-N-(1-isobutyl-3-methylbutyl)-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C / Cooling with ice

2.1: trifluoroacetic acid / dichloromethane / 1.5 h / 20 °C

3.1: triethylamine / dichloromethane / 18 h / 20 °C

4.1: sodium hydroxide / methanol / 1 h / 60 °C

5.1: diphenylphosphoranyl azide / toluene / 2 h / 90 °C

5.2: 24 h / 90 °C

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 50 °C

With diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.bmc.2013.06.057

Reference yield:

: 1448902-64-4
methyl (3R,5S)-5-[(1-isobutyl-3-methylbutyl)carbamoyl]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate

: 1448902-66-6
(3S,5R)-5-amino-N-(1-isobutyl-3-methylbutyl)-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydroxide / methanol / 1 h / 60 °C

2.1: diphenylphosphoranyl azide / toluene / 2 h / 90 °C

2.2: 24 h / 90 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 50 °C

With diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; sodium hydroxide; In tetrahydrofuran; methanol; toluene;
DOI:10.1016/j.bmc.2013.06.057