7,7-Bis-((S)-4-phenyl-4,5-dihydro-oxazol-2-yl)-heptanoic acid (S)-((2R,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-(6-methoxy-quinolin-4-yl)-methyl ester

Base Information

• Chemical Name: 7,7-Bis-((S)-4-phenyl-4,5-dihydro-oxazol-2-yl)-heptanoic acid (S)-((2R,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-(6-methoxy-quinolin-4-yl)-methyl ester
• CAS No.: 342814-68-0
• Molecular Formula: C₄₅H₅₂N₄O₅
• Molecular Weight: 728.932

Synonyms:7,7-Bis-((S)-4-phenyl-4,5-dihydro-oxazol-2-yl)-heptanoic acid (S)-((2R,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-(6-methoxy-quinolin-4-yl)-methyl ester

Chemical Property of 7,7-Bis-((S)-4-phenyl-4,5-dihydro-oxazol-2-yl)-heptanoic acid (S)-((2R,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-(6-methoxy-quinolin-4-yl)-methyl ester

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Technology Process of 7,7-Bis-((S)-4-phenyl-4,5-dihydro-oxazol-2-yl)-heptanoic acid (S)-((2R,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-(6-methoxy-quinolin-4-yl)-methyl ester

There total 3 articles about 7,7-Bis-((S)-4-phenyl-4,5-dihydro-oxazol-2-yl)-heptanoic acid (S)-((2R,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-(6-methoxy-quinolin-4-yl)-methyl 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: 55.0%

(S,S)-2,2'-methylenebis(4-phenyl-2-oxazoline) (132098-59-0) + 6-Bromo-hexanoic acid (S)-((2R,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-(6-methoxy-quinolin-4-yl)-methyl ester (342814-67-9) → 7,7-Bis-((S)-4-phenyl-4,5-dihydro-oxazol-2-yl)-heptanoic acid (S)-((2R,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-(6-methoxy-quinolin-4-yl)-methyl ester (342814-68-0)

Guidance literature:

(S,S)-2,2'-methylenebis(4-phenyl-2-oxazoline); With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; diisopropylamine; In dichloromethane; at -50 ℃; for 1.5h;

6-Bromo-hexanoic acid (S)-((2R,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-(6-methoxy-quinolin-4-yl)-methyl ester; In tetrahydrofuran; at 20 ℃; for 15h; Further stages.;

DOI:10.1002/1099-0690(200103)2001:6<1045::AID-EJOC1045>3.0.CO;2-I

Reference yield:

6-bromohexanoyl chloride (22809-37-6) → 7,7-Bis-((S)-4-phenyl-4,5-dihydro-oxazol-2-yl)-heptanoic acid (S)-((2R,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-(6-methoxy-quinolin-4-yl)-methyl ester (342814-68-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 100 percent / Et₃N / CH₂Cl₂ / 15 h / 20 °C

2.1: nBuLi in hexane; TMEDA; (iPr)2NH / various solvent(s); CH₂Cl₂ / 1.5 h / -50 °C

2.2: 55 percent / tetrahydrofuran; various solvent(s) / 15 h / 20 °C

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; triethylamine; diisopropylamine; In dichloromethane;

DOI:10.1002/1099-0690(200103)2001:6<1045::AID-EJOC1045>3.0.CO;2-I

Reference yield:

hydroquinidine (1435-55-8) → 7,7-Bis-((S)-4-phenyl-4,5-dihydro-oxazol-2-yl)-heptanoic acid (S)-((2R,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-(6-methoxy-quinolin-4-yl)-methyl ester (342814-68-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 100 percent / Et₃N / CH₂Cl₂ / 15 h / 20 °C

2.1: nBuLi in hexane; TMEDA; (iPr)2NH / various solvent(s); CH₂Cl₂ / 1.5 h / -50 °C

2.2: 55 percent / tetrahydrofuran; various solvent(s) / 15 h / 20 °C

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; triethylamine; diisopropylamine; In dichloromethane;

DOI:10.1002/1099-0690(200103)2001:6<1045::AID-EJOC1045>3.0.CO;2-I

upstream raw materials:

(S,S)-2,2'-methylenebis(4-phenyl-2-oxazoline)

6-Bromo-hexanoic acid (S)-((2R,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-(6-methoxy-quinolin-4-yl)-methyl ester

6-bromohexanoyl chloride

hydroquinidine

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