1,1-dimethylethyl {(1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-[(3-fluorophenyl)methyl]ethyl}carbamate

Base Information

• Chemical Name: 1,1-dimethylethyl {(1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-[(3-fluorophenyl)methyl]ethyl}carbamate
• CAS No.: 1201923-48-9
• Molecular Formula: C₂₂H₂₃FN₂O₄
• Molecular Weight: 398.434
• Mol file: 1201923-48-9.mol

Synonyms:1,1-dimethylethyl {(1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-[(3-fluorophenyl)methyl]ethyl}carbamate

Chemical Property of 1,1-dimethylethyl {(1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-[(3-fluorophenyl)methyl]ethyl}carbamate

Chemical Property:

• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

(S)-tert-Butyl(1-(1,3-dioxoisoindolin-2-yl)-3-(3-fluorophenyl)propan-2-yl)carbamate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,1-dimethylethyl {(1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-[(3-fluorophenyl)methyl]ethyl}carbamate

There total 3 articles about 1,1-dimethylethyl {(1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-[(3-fluorophenyl)methyl]ethyl}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: 67.2%

phthalimide (136918-14-4,85-41-6) + [(S)-2-(3-fluoro-phenyl)-1-hydroxymethyl-ethyl]carbamic acid tert-butyl ester → 1,1-dimethylethyl {(1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-[(3-fluorophenyl)methyl]ethyl}carbamate (1201923-48-9)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 0.5h; Cooling with ice;

Reference yield:

phthalimide (136918-14-4,85-41-6) + tert-butyl [(1S)-1-(3-fluorobenzyl)-2-hydroxyethyl]carbamate (944470-56-8,1199781-37-7) → 1,1-dimethylethyl {(1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-[(3-fluorophenyl)methyl]ethyl}carbamate (1201923-48-9)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 - 25 ℃; for 1h;

Reference yield:

N-Boc-3-fluoro-L-phenylalanine (114873-01-7,114873-11-9) → 1,1-dimethylethyl {(1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-[(3-fluorophenyl)methyl]ethyl}carbamate (1201923-48-9)

Guidance literature:

Multi-step reaction with 2 steps

1: borane-THF / tetrahydrofuran

2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran

With borane-THF; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; 2: |Mitsunobu Displacement;

DOI:10.1358/dof.2014.039.08.2177902

upstream raw materials:

phthalimide

tert-butyl [(1S)-1-(3-fluorobenzyl)-2-hydroxyethyl]carbamate

N-Boc-3-fluoro-L-phenylalanine

Downstream raw materials:

2-[(2S)-2-amino-3-(3-fluorophenyl)propyl]-1H-isoindole-1,3(2H)-dione hydrochloride

N-{(1S)-2-amino-1-[(3-fluorophenyl)methyl] ethyl}-5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide

5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-N-{(1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-[(3-fluorophenyl)methyl]ethyl}-2-thiophenecarboxamide

2-[(2S)-2-amino-3-(3-fluorophenyl)propyl]-1H-isoindole-1,3(2H)-dione

Refernces

• 1、 -. "ISOINDOLINONE AND PYRROLOPYRIDINONE DERIVATIVES AS AKT INHIBITORS". Paragraph 0248-0250. . Retrieved 2013/04/24.
• 2、 -. "INHIBITORS OF AKT ACTIVITY". Page/Page column 33; 34. . Retrieved 2010/01/30.