Benzoic acid (S)-1-((4R,5S)-3,5-dimethyl-2-oxo-oxazolidin-4-yl)-2-[1,3]dioxolan-2-yl-ethyl ester

Base Information

• Chemical Name: Benzoic acid (S)-1-((4R,5S)-3,5-dimethyl-2-oxo-oxazolidin-4-yl)-2-[1,3]dioxolan-2-yl-ethyl ester
• CAS No.: 232942-80-2
• Molecular Formula: C₁₇H₂₁NO₆
• Molecular Weight: 335.357
• Mol file: 232942-80-2.mol

Synonyms:Benzoic acid (S)-1-((4R,5S)-3,5-dimethyl-2-oxo-oxazolidin-4-yl)-2-[1,3]dioxolan-2-yl-ethyl ester

Chemical Property of Benzoic acid (S)-1-((4R,5S)-3,5-dimethyl-2-oxo-oxazolidin-4-yl)-2-[1,3]dioxolan-2-yl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (S)-1-((4R,5S)-3,5-dimethyl-2-oxo-oxazolidin-4-yl)-2-[1,3]dioxolan-2-yl-ethyl ester

There total 7 articles about Benzoic acid (S)-1-((4R,5S)-3,5-dimethyl-2-oxo-oxazolidin-4-yl)-2-[1,3]dioxolan-2-yl-ethyl 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: 65.0%

Benzoyl-carbamic acid (S)-1-((2S,3S)-3-[1,3]dioxolan-2-ylmethyl-oxiranyl)-ethyl ester (232942-78-8) + methyl iodide (74-88-4) → Benzoic acid (S)-1-((4R,5S)-3,5-dimethyl-2-oxo-oxazolidin-4-yl)-2-[1,3]dioxolan-2-yl-ethyl ester (232942-80-2)

Guidance literature:

Benzoyl-carbamic acid (S)-1-((2S,3S)-3-[1,3]dioxolan-2-ylmethyl-oxiranyl)-ethyl ester; With sodium hexamethyldisilazane; In tetrahydrofuran; at 20 ℃; for 9h;

methyl iodide; In tetrahydrofuran; for 1h;

DOI:10.1016/S0040-4039(99)00906-5

Reference yield:

2-bromo-2-(2-ethyl)dioxolane (18742-02-4) → Benzoic acid (S)-1-((4R,5S)-3,5-dimethyl-2-oxo-oxazolidin-4-yl)-2-[1,3]dioxolan-2-yl-ethyl ester (232942-80-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 92 percent / NaH / dimethylformamide / 12 h / 20 °C

2.1: 89 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 6 h / 20 °C

3.1: 80 percent / KHMDS / 1,2-dimethoxy-ethane / 14 h / -55 - 0 °C

4.1: 91 percent / 5 percent HF(aq) / acetonitrile / 0.83 h

5.1: L-(+)-DET; Ti(i-PrO)4; TBHP, 4 angstroem mol. sieves / CH₂Cl₂ / 13 h / -25 °C

6.1: tetrahydrofuran / 0.5 h

7.1: NaHMDS / tetrahydrofuran / 9 h / 20 °C

7.2: 65 percent / tetrahydrofuran / 1 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; 4 A molecular sieve; hydrogen fluoride; sodium hexamethyldisilazane; potassium hexamethylsilazane; sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Alkylation / 2.1: Oxidation / 3.1: Condensation / 4.1: desilylation / 5.1: Epoxidation / 6.1: Addition / 7.1: Metallation / 7.2: Methylation;

DOI:10.1016/S0040-4039(99)00906-5

Reference yield:

(E)-(S)-5-[1,3]Dioxolan-2-yl-pent-3-en-2-ol (232942-74-4) → Benzoic acid (S)-1-((4R,5S)-3,5-dimethyl-2-oxo-oxazolidin-4-yl)-2-[1,3]dioxolan-2-yl-ethyl ester (232942-80-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: L-(+)-DET; Ti(i-PrO)4; TBHP, 4 angstroem mol. sieves / CH₂Cl₂ / 13 h / -25 °C

2.1: tetrahydrofuran / 0.5 h

3.1: NaHMDS / tetrahydrofuran / 9 h / 20 °C

3.2: 65 percent / tetrahydrofuran / 1 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; 4 A molecular sieve; sodium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; 1.1: Epoxidation / 2.1: Addition / 3.1: Metallation / 3.2: Methylation;

DOI:10.1016/S0040-4039(99)00906-5

upstream raw materials:

Benzoyl-carbamic acid (S)-1-((2S,3S)-3-[1,3]dioxolan-2-ylmethyl-oxiranyl)-ethyl ester

methyl iodide

2-bromo-2-(2-ethyl)dioxolane

(E)-(S)-5-[1,3]Dioxolan-2-yl-pent-3-en-2-ol