(4S)-4-(1-methylethyl)-5,5-diphenyl-3-{(2S)-2-(phthalimidomethyl)-3-[(triphenylmethyl)sulfanyl]propanoyl}oxazolidin-2-one

Base Information

• Chemical Name: (4S)-4-(1-methylethyl)-5,5-diphenyl-3-{(2S)-2-(phthalimidomethyl)-3-[(triphenylmethyl)sulfanyl]propanoyl}oxazolidin-2-one
• CAS No.: 847153-44-0
• Molecular Formula: C₄₉H₄₂N₂O₅S
• Molecular Weight: 770.949
• Mol file: 847153-44-0.mol

Synonyms:(4S)-4-(1-methylethyl)-5,5-diphenyl-3-{(2S)-2-(phthalimidomethyl)-3-[(triphenylmethyl)sulfanyl]propanoyl}oxazolidin-2-one

Chemical Property of (4S)-4-(1-methylethyl)-5,5-diphenyl-3-{(2S)-2-(phthalimidomethyl)-3-[(triphenylmethyl)sulfanyl]propanoyl}oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-4-(1-methylethyl)-5,5-diphenyl-3-{(2S)-2-(phthalimidomethyl)-3-[(triphenylmethyl)sulfanyl]propanoyl}oxazolidin-2-one

There total 5 articles about (4S)-4-(1-methylethyl)-5,5-diphenyl-3-{(2S)-2-(phthalimidomethyl)-3-[(triphenylmethyl)sulfanyl]propanoyl}oxazolidin-2-one 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: 71.0%

triphenylmethanethiol (3695-77-0) + (S)-3-<(R)-3-hydroxy-1-oxo-2-(phthalimidomethyl)propyl>-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one (218800-60-3) → (4S)-4-(1-methylethyl)-5,5-diphenyl-3-{(2S)-2-(phthalimidomethyl)-3-[(triphenylmethyl)sulfanyl]propanoyl}oxazolidin-2-one (847153-44-0) + (4S)-4-(1-methylethyl)-5,5-diphenyl-3-{(2R)-2-(phthalimidomethyl)-3-[(triphenylmethyl)sulfanyl]propanoyl}oxazolidin-2-one

Guidance literature:

With tributylphosphine; azidodicarboxylic dipiperidide; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1002/hlca.200490280

Reference yield:

phthalic anhydride (85-44-9) → (4S)-4-(1-methylethyl)-5,5-diphenyl-3-{(2S)-2-(phthalimidomethyl)-3-[(triphenylmethyl)sulfanyl]propanoyl}oxazolidin-2-one (847153-44-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 94 percent / 2 h / 150 °C

2.1: 100 percent / (COCl)2 / CH₂Cl₂; dioxane / 20 °C

3.1: BuLi / tetrahydrofuran; hexane / cooling

3.2: 86 percent / tetrahydrofuran; hexane / 48 h / 20 °C

4.1: NEt₃; TiCl₄ / CH₂Cl₂ / 0.5 h / -10 °C

4.2: 89 percent / TiCl₄ / CH₂Cl₂ / -10 - 0 °C

5.1: 71 percent / Bu₃P; azidodicarboxylic dipiperidide / tetrahydrofuran / 1 h / 20 °C

With n-butyllithium; oxalyl dichloride; tributylphosphine; azidodicarboxylic dipiperidide; titanium tetrachloride; triethylamine; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane;

DOI:10.1002/hlca.200490280

Reference yield:

3-phthalimidopropionyl chloride (17137-11-0) → (4S)-4-(1-methylethyl)-5,5-diphenyl-3-{(2S)-2-(phthalimidomethyl)-3-[(triphenylmethyl)sulfanyl]propanoyl}oxazolidin-2-one (847153-44-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: BuLi / tetrahydrofuran; hexane / cooling

1.2: 86 percent / tetrahydrofuran; hexane / 48 h / 20 °C

2.1: NEt₃; TiCl₄ / CH₂Cl₂ / 0.5 h / -10 °C

2.2: 89 percent / TiCl₄ / CH₂Cl₂ / -10 - 0 °C

3.1: 71 percent / Bu₃P; azidodicarboxylic dipiperidide / tetrahydrofuran / 1 h / 20 °C

With n-butyllithium; tributylphosphine; azidodicarboxylic dipiperidide; titanium tetrachloride; triethylamine; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1002/hlca.200490280

upstream raw materials:

triphenylmethanethiol

(S)-3-<(R)-3-hydroxy-1-oxo-2-(phthalimidomethyl)propyl>-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one

phthalic anhydride

3-phthalimidopropionyl chloride

Downstream raw materials:

2-(trimethylsilyl)ethyl (S)-2-(phthalimidomethyl)-3-[(triphenylmethyl)sulfanyl]propanoate

2-(trimethylsilyl)ethyl (S)-2-({[(tert-butoxy)carbonyl]amino}methyl)-3-[(triphenylmethyl)sulfanyl]propanoate

2-(trimethylsilyl)ethyl (S)-2-aminomethyl-3-[(triphenylmethyl)sulfanyl]propanoate

(S)-2-({[(tert-butoxy)carbonyl]amino}methyl)-3-[(triphenylmethyl)sulfanyl]propanoic acid