tert-butyl ((S)-2-(4-chlorophenyl)-3-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-oxopropyl)carbamate

Base Information

• Chemical Name: tert-butyl ((S)-2-(4-chlorophenyl)-3-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-oxopropyl)carbamate
• CAS No.: 1001270-26-3
• Molecular Formula: C₂₆H₃₄ClN₅O₄
• Molecular Weight: 516.04
• Mol file: 1001270-26-3.mol

Synonyms:tert-butyl ((S)-2-(4-chlorophenyl)-3-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-oxopropyl)carbamate

Chemical Property of tert-butyl ((S)-2-(4-chlorophenyl)-3-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-oxopropyl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl ((S)-2-(4-chlorophenyl)-3-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-oxopropyl)carbamate

There total 23 articles about tert-butyl ((S)-2-(4-chlorophenyl)-3-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-oxopropyl)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%

(S)-3-((tert-butoxycarbonyl)amino)-2-(4-chlorophenyl)propanoic acid (1001180-04-6) + (5R,7R)-5-methyl-4-(piperazin-1-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-ol dihydrochloride salt → tert-butyl ((S)-2-(4-chlorophenyl)-3-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-oxopropyl)carbamate (1001270-26-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1016/j.chembiol.2019.11.014

Reference yield:

tert-butyl 4-((5R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-piperazine-1-carboxylate (1001180-15-9) → tert-butyl ((S)-2-(4-chlorophenyl)-3-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-oxopropyl)carbamate (1001270-26-3)

Guidance literature:

Multi-step reaction with 4 steps

1: chiral separation HPLC (Chiralcel ODH column) / hexane; ethanol / Resolution of diastereomers

2: lithium hydroxide / tetrahydrofuran / 6 h / 20 °C

3: hydrogenchloride / dichloromethane; 1,4-dioxane / 6 h

4: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 1 h / 20 °C

With hydrogenchloride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; ethanol; hexane; dichloromethane;

Reference yield:

tert-butyl 4-((5R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-piperazine-1-carboxylate (1001180-18-2) → tert-butyl ((S)-2-(4-chlorophenyl)-3-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-oxopropyl)carbamate (1001270-26-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

1.2: 0.5 h / -78 - 20 °C

2.1: triethylamine; formic acid / Ru catalyst / dichloromethane / 18 h / Inert atmosphere

3.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 6 h

4.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 1 h / 20 °C

With hydrogenchloride; formic acid; oxalyl dichloride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; Ru catalyst; In 1,4-dioxane; dichloromethane;

upstream raw materials:

(S)-3-((tert-butoxycarbonyl)amino)-2-(4-chlorophenyl)propanoic acid

ethyl (2R)-2-methyl-5-(propan-2-ylidene)cyclopentanecarboxylate

(2R)-2-methyl-5-oxocyclopentanecarboxylic acid ethyl ester

tert-butyl 2,4-dimethoxybenzyl(methoxymethyl)carbamate

Downstream raw materials:

C₂₇H₃₆ClN₅O₃