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)(isopropyl)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)(isopropyl)carbamate
• CAS No.: 1001270-64-9
• Molecular Formula: C₂₉H₄₀ClN₅O₄
• Molecular Weight: 558.121
• Mol file: 1001270-64-9.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)(isopropyl)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)(isopropyl)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)(isopropyl)carbamate

There total 64 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)(isopropyl)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: 87.0%

(S)-3-((tert-butoxycarbonyl)(isopropyl)amino)-2-(4-chlorophenyl)propionic acid (1001179-33-4) + (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)(isopropyl)carbamate (1001270-64-9)

Guidance literature:

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; at 0 - 20 ℃; for 4h;

DOI:10.1021/jm301024w

Reference yield: 86.0%

(S)-3-((tert-butoxycarbonyl)(isopropyl)amino)-2-(4-chlorophenyl)propionic acid (1001179-33-4) + tert-butyl 4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]-pyrimidin-4-yl)piperazine-1-carboxylate (1001180-45-5) → 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)(isopropyl)carbamate (1001270-64-9)

Guidance literature:

tert-butyl 4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]-pyrimidin-4-yl)piperazine-1-carboxylate; With 4-methyl-morpholine; hydrogenchloride; In isopropyl alcohol; at 55 - 65 ℃; Inert atmosphere;

With 4-methyl-morpholine; In isopropyl alcohol; at 5 - 25 ℃; for 0.5h;

(S)-3-((tert-butoxycarbonyl)(isopropyl)amino)-2-(4-chlorophenyl)propionic acid; With propylphosphonic anhydride; In isopropyl alcohol; at 0 - 20 ℃;

Reference yield:

(5R,7R)-5-methyl-4-(piperazin-1-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-ol (1001382-23-5) + sodium (S)-3-((tert-butoxycarbonyl)(isopropyl)amino)-2-(4-chlorophenyl)propanoate → 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)(isopropyl)carbamate (1001270-64-9)

Guidance literature:

(5R,7R)-5-methyl-4-(piperazin-1-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-ol; With 4-methyl-morpholine; In isopropyl alcohol; at 10 - 15 ℃; for 0.5h;

sodium (S)-3-((tert-butoxycarbonyl)(isopropyl)amino)-2-(4-chlorophenyl)propanoate; With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In isopropyl alcohol; toluene; at 5 ℃;

upstream raw materials:

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

(4-chloro-phenyl)-acetic acid methyl ester

methyl 2-(4-chlorophenyl)acrylate

methyl 2-(4-chlorophenyl)-3-hydroxypropanoate

Downstream raw materials:

(2S)-2-(4-chlorophenyl)-1-[4-[(5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(propan-2-yiamino)propan-1-one

Refernces

• 1、 -. "PROCESSES FOR THE PREPARATION OF PYRIMIDINYLCYCLOPENTANE COMPOUNDS". . . Retrieved 2015/06/03.
• 2、 Remarchuk, Travis,St-Jean, Frederic,Carrera, Diane,Savage, Scott,Yajima, Herbert,Wong, Brian,Babu, Srinivasan,Deese, Alan,Stults, Jeffrey,Dong, Michael W.,Askin, David,Lane, Jonathan W.,Spencer, Keith L.. "Synthesis of Akt inhibitor ipatasertib. part 2. Total synthesis and first kilogram scale-up". supporting information. p. 1652 - 1666. Retrieved 2015/02/19.