(3S,5R)-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-N-[(1R)-2-hydroxy-1-isobutyl-3-methylbutyl]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxamide

Base Information

• Chemical Name: (3S,5R)-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-N-[(1R)-2-hydroxy-1-isobutyl-3-methylbutyl]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxamide
• CAS No.: 1448902-63-3
• Molecular Formula: C₃₃H₄₆ClN₅O₇S
• Molecular Weight: 692.277
• Mol file: 1448902-63-3.mol

Synonyms:(3S,5R)-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-N-[(1R)-2-hydroxy-1-isobutyl-3-methylbutyl]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxamide

Chemical Property of (3S,5R)-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-N-[(1R)-2-hydroxy-1-isobutyl-3-methylbutyl]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5R)-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-N-[(1R)-2-hydroxy-1-isobutyl-3-methylbutyl]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxamide

There total 20 articles about (3S,5R)-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-N-[(1R)-2-hydroxy-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: 72.0%

(3S,5R)-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylic acid (1263198-07-7) + (4R)-4-amino-2,6-dimethylheptan-3-ol hydrochloride (1448902-03-1) → (3S,5R)-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-N-[(1R)-2-hydroxy-1-isobutyl-3-methylbutyl]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxamide (1448902-63-3)

Guidance literature:

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 18h; Cooling with ice;

DOI:10.1016/j.bmc.2013.06.057

Reference yield:

(3S,5R)-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylic acid (1263198-07-7) + C9H21NO (944141-72-4,944146-22-9) → (3S,5R)-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-N-[(1R)-2-hydroxy-1-isobutyl-3-methylbutyl]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxamide (1448902-63-3)

Guidance literature:

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 5h;

DOI:10.1016/j.bmcl.2012.09.103

Reference yield:

(3S,5R)-1-(tert-butoxycarbonyl)-3-(methoxycarbonyl)piperidine-5-carboxylic acid (534572-20-8) → (3S,5R)-5-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-N-[(1R)-2-hydroxy-1-isobutyl-3-methylbutyl]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxamide (1448902-63-3)

Guidance literature:

Multi-step reaction with 14 steps

1: diphenylphosphoranyl azide; triethylamine / toluene / 15 h / 90 °C

2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

3: triethylamine / dichloromethane / 1 h / 20 °C

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; morpholine / tetrahydrofuran / 1 h / 20 °C

5: dichloromethane / 2 h / 20 °C

6: N-chloro-succinimide / dichloromethane / 2 h / 20 °C

7: 18 h / 60 °C

8: hydrogenchloride / dichloromethane; water / 4 h / 40 °C

9: thionyl chloride / 1 h / 20 °C

10: acetic acid / toluene / 2 h / 110 °C

11: sodium cyanoborohydride / 6 h / 20 °C

12: triethylamine / dichloromethane / 5 h / 0 - 40 °C

13: sodium hydroxide; water / methanol / 0.5 h / 50 °C

14: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 5 h / 20 °C

With morpholine; hydrogenchloride; N-chloro-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; diphenylphosphoranyl azide; water; sodium cyanoborohydride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1: |Curtius Rearrangement;

DOI:10.1016/j.bmcl.2012.09.103

upstream raw materials:

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

C₁₆H₂₆N₂O₆

C₁₇H₂₁N₃O₈S

C₁₃H₁₇N₃O₆S

Downstream raw materials:

C₂₇H₄₃ClN₄O₃