(S)-4-(1-methylethyl)-3-<1-oxo-3-phthalimidopropyl>-5,5-diphenyloxazolidin-2-one

Base Information

• Chemical Name: (S)-4-(1-methylethyl)-3-<1-oxo-3-phthalimidopropyl>-5,5-diphenyloxazolidin-2-one
• CAS No.: 218800-38-5
• Molecular Formula: C₂₉H₂₆N₂O₅
• Molecular Weight: 482.536
• Mol file: 218800-38-5.mol

Synonyms:(S)-4-(1-methylethyl)-3-<1-oxo-3-phthalimidopropyl>-5,5-diphenyloxazolidin-2-one

Chemical Property of (S)-4-(1-methylethyl)-3-<1-oxo-3-phthalimidopropyl>-5,5-diphenyloxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-(1-methylethyl)-3-<1-oxo-3-phthalimidopropyl>-5,5-diphenyloxazolidin-2-one

There total 10 articles about (S)-4-(1-methylethyl)-3-<1-oxo-3-phthalimidopropyl>-5,5-diphenyloxazolidin-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: 89.0%

3-phthalimidopropionyl chloride (17137-11-0) + (S)-5,5-Diphenyl-4-isopropyl-1,3-oxazolidin-2-one (184346-45-0) → (S)-4-(1-methylethyl)-3-<1-oxo-3-phthalimidopropyl>-5,5-diphenyloxazolidin-2-one (218800-38-5)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1002/(SICI)1522-2675(19981111)81:11<2093::AID-HLCA2093>3.0.CO;2-X

Reference yield:

3-phthalimidopropanoic acid (3339-73-9) → (S)-4-(1-methylethyl)-3-<1-oxo-3-phthalimidopropyl>-5,5-diphenyloxazolidin-2-one (218800-38-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 100 percent / (COCl)2 / CH₂Cl₂; dioxane / 20 °C

2.1: BuLi / tetrahydrofuran; hexane / cooling

2.2: 86 percent / tetrahydrofuran; hexane / 48 h / 20 °C

With n-butyllithium; oxalyl dichloride; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane;

DOI:10.1002/hlca.200490280

Reference yield:

(S)-4-(1-methylethyl)-3-(1-oxopropyl)-5,5-diphenyloxazolidin-2-one (213887-84-4) → (S)-4-(1-methylethyl)-3-<1-oxo-3-phthalimidopropyl>-5,5-diphenyloxazolidin-2-one (218800-38-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.)LDA, ZnBr₂ / 1.)THF, -78 deg C, 60 min; 2.)THF, -15 deg C, 24 h

2: 92 percent / LiBr, DBU / tetrahydrofuran / 4 h / Ambient temperature

3: 89 percent / BuLi / tetrahydrofuran / 0 - 20 °C

With n-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium bromide; zinc dibromide; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1002/(SICI)1522-2675(19981111)81:11<2093::AID-HLCA2093>3.0.CO;2-X

upstream raw materials:

3-phthalimidopropionyl chloride

(S)-5,5-Diphenyl-4-isopropyl-1,3-oxazolidin-2-one

phthalic anhydride

3-phthalimidopropanoic acid

Downstream raw materials:

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

2-({[(2R)-2-carboxy-3-(1,1-dimethylethoxy)propyl]amino}carbonyl)benzoic acid

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

benzyl (R)-3-(tert-butoxy)-2-(phthalimidomethyl)propanoate