methyl 2-(tert-butoxy)-2-((S)-4-(2,3-dihydropyrano[4,3,2-de]quinolin-7-yl)-2-methylquinolin-3-yl)acetate

Base Information

• Chemical Name: methyl 2-(tert-butoxy)-2-((S)-4-(2,3-dihydropyrano[4,3,2-de]quinolin-7-yl)-2-methylquinolin-3-yl)acetate
• CAS No.: 1402714-51-5
• Molecular Formula: C₂₈H₂₈N₂O₄
• Molecular Weight: 456.541
• Mol file: 1402714-51-5.mol

Synonyms:

Chemical Property of methyl 2-(tert-butoxy)-2-((S)-4-(2,3-dihydropyrano[4,3,2-de]quinolin-7-yl)-2-methylquinolin-3-yl)acetate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

3-Quinolineaceticacid,4-(2,3-dihydropyrano[4,3,2-de]quinolin-7-yl)-α-(1,1-dimethylethoxy)-2-methyl-,methylester,(αS,4R)- ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-(tert-butoxy)-2-((S)-4-(2,3-dihydropyrano[4,3,2-de]quinolin-7-yl)-2-methylquinolin-3-yl)acetate

There total 54 articles about methyl 2-(tert-butoxy)-2-((S)-4-(2,3-dihydropyrano[4,3,2-de]quinolin-7-yl)-2-methylquinolin-3-yl)acetate 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: 95.0%

tert-Butyl 2,2,2-trichloroacetimidate (98946-18-0) + methyl 2-((R)-4-(2,3-dihydropyrano[4,3,2-de]quinolin-7-yl)-2-methylquinolin-3-yl)-2-hydroxyacetate → methyl 2-(tert-butoxy)-2-((R)-4-(2,3-dihydropyrano[4,3,2-de]quinolin-7-yl)-2-methylquinolin-3-yl)acetate (1402714-51-5)

Guidance literature:

With bis(trifluoromethanesulfonyl)amide; In n-heptane; dichloromethane; at 40 ℃; Solvent; Temperature; Reagent/catalyst; Inert atmosphere;

DOI:10.1002/anie.201501575

Reference yield: 90.5%

tert-Butyl 2,2,2-trichloroacetimidate (98946-18-0) + C24H20N2O4 → C28H28N2O4 (1402714-51-5)

Guidance literature:

bis(trifluoromethanesulfonyl)amide; In fluorobenzene; dichloromethane; at 35 - 41 ℃; Inert atmosphere; Industry scale;

Reference yield:

acetonedicarboxylic acid (542-05-2) → C28H28N2O4 (1402714-51-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 40 °C / Inert atmosphere

2.1: fluorobenzene / 4 h / 35 - 37 °C / Inert atmosphere

2.2: 2.5 h / 23 - 45 °C

3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / isopropyl alcohol; toluene; tetrahydrofuran / 4.5 h / 0 - 25 °C

3.2: 40 °C

4.1: trichlorophosphate / acetonitrile / 65 - 75 °C

5.1: trifluoroacetic acid; zinc / 1 h / 60 - 70 °C

6.1: n-butyllithium / toluene; hexane / 1 h / -50 - -45 °C

6.2: 0.5 h / 10 °C / Industry scale

6.3: 0.5 h / 10 - 20 °C

7.1: sodium carbonate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (S)-3-tert-butyl-4-(2,6-dimethoxyphenyl)-2,3-dihydrobenzo[d][1,3]oxaphosphole / water; pentan-1-ol / 60 - 63 °C / Industry scale; Inert atmosphere

8.1: bis(trifluoromethanesulfonyl)amide / dichloromethane; fluorobenzene / 35 - 41 °C / Inert atmosphere; Industry scale

With n-butyllithium; sodium carbonate; sodium bis(2-methoxyethoxy)aluminium dihydride; trifluoroacetic acid; zinc; trichlorophosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (S)-3-tert-butyl-4-(2,6-dimethoxyphenyl)-2,3-dihydrobenzo[d][1,3]oxaphosphole; bis(trifluoromethanesulfonyl)amide; In tetrahydrofuran; fluorobenzene; hexane; dichloromethane; pentan-1-ol; water; isopropyl alcohol; toluene; acetonitrile; 7.1: Suzuki Coupling;

upstream raw materials:

tert-Butyl 2,2,2-trichloroacetimidate

acetonedicarboxylic acid

2,6-dioxo-3,6-dihydro-2H-pyran-4-yl acetate

4-hydroxy-2-methylquinoline

Downstream raw materials:

BI-224436

2-(tert-butoxy)-2-((R)-4-(2,3-dihydropyrano[4,3,2-de]quinolin-7-yl)-2-methylquinolin-3-yl)acetic acid

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF AN HIV INTEGRASE INHIBITOR". Page/Page column 67-68. . Retrieved 2012/10/18.