[(R)-1-(2,2-diethoxyethyl)-2-oxo-3-(3-p-tolylureido)-2,3-dihydro-1H-indol-3-yl]acetic acid (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl ester

Base Information

• Chemical Name: [(R)-1-(2,2-diethoxyethyl)-2-oxo-3-(3-p-tolylureido)-2,3-dihydro-1H-indol-3-yl]acetic acid (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl ester
• CAS No.: 159883-92-8
• Molecular Formula: C₃₄H₄₇N₃O₆
• Molecular Weight: 593.764
• Mol file: 159883-92-8.mol

Synonyms:[(R)-1-(2,2-diethoxyethyl)-2-oxo-3-(3-p-tolylureido)-2,3-dihydro-1H-indol-3-yl]acetic acid (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl ester

Chemical Property of [(R)-1-(2,2-diethoxyethyl)-2-oxo-3-(3-p-tolylureido)-2,3-dihydro-1H-indol-3-yl]acetic acid (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(R)-1-(2,2-diethoxyethyl)-2-oxo-3-(3-p-tolylureido)-2,3-dihydro-1H-indol-3-yl]acetic acid (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl ester

There total 4 articles about [(R)-1-(2,2-diethoxyethyl)-2-oxo-3-(3-p-tolylureido)-2,3-dihydro-1H-indol-3-yl]acetic acid (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl ester 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: 83.0%

N-[1-(2,2-diethoxyethyl)-2,3-dihydro-2-oxo-1H-indol-3-yl]-N'-(4-methylphenyl)urea (195451-17-3) + (1R,2S,5R)-menthol bromoacetate (16832-20-5,32815-12-6,55284-67-8) → [(R)-1-(2,2-diethoxyethyl)-2-oxo-3-(3-p-tolylureido)-2,3-dihydro-1H-indol-3-yl]acetic acid (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl ester (159883-92-8) + [(S)-1-(2,2-diethoxyethyl)-2-oxo-3-(3-p-tolylureido)-2,3-dihydro-1H-indol-3-yl]acetic acid (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl ester

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 5h;

DOI:10.1021/jo061541v

Reference yield:

1-(2,2-diethoxyethyl)-1H-indole-2,3-dione 3-(O-methyloxime) (159884-54-5) → [(R)-1-(2,2-diethoxyethyl)-2-oxo-3-(3-p-tolylureido)-2,3-dihydro-1H-indol-3-yl]acetic acid (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl ester (159883-92-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrogen / palladium on carbon / acetonitrile / 6 h / 20 °C / atmospheric pressure

1.2: 109 g / acetonitrile / 1 h / 20 °C

2.1: 83 percent / LiHMDS / tetrahydrofuran / 5 h / 0 °C

With hydrogen; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jo061541v

Reference yield:

indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) → [(R)-1-(2,2-diethoxyethyl)-2-oxo-3-(3-p-tolylureido)-2,3-dihydro-1H-indol-3-yl]acetic acid (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl ester (159883-92-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 100 percent / dipotassium hydrogen phosphate / methanol / 2 h / 20 °C

2.1: 127 g / potassium tert-butoxide / N,N-dimethyl-acetamide / 4 h / 110 °C

3.1: hydrogen / palladium on carbon / acetonitrile / 6 h / 20 °C / atmospheric pressure

3.2: 109 g / acetonitrile / 1 h / 20 °C

4.1: 83 percent / LiHMDS / tetrahydrofuran / 5 h / 0 °C

With dipotassium hydrogenphosphate; potassium tert-butylate; hydrogen; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl acetamide; acetonitrile;

DOI:10.1021/jo061541v

upstream raw materials:

N-[1-(2,2-diethoxyethyl)-2,3-dihydro-2-oxo-1H-indol-3-yl]-N'-(4-methylphenyl)urea

(1R,2S,5R)-menthol bromoacetate

1-(2,2-diethoxyethyl)-1H-indole-2,3-dione 3-(O-methyloxime)

indole-2,3-dione

Downstream raw materials:

AG 041R

[(R)-2-oxo-1-(2-oxo-ethyl)-3-(3-p-tolylureido)-2,3-dihydro-1H-indol-3-yl]-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

[1-(2,2-diethoxy-ethyl)-2-oxo-3-(3-p-tolyl-ureido)-2,3-dihydro-1H-indol-3-yl]-acetic acid