3-<4-(1,3-dioxolan-2-yl)-1-oxo-3(R)-phenylbutyl>-4(S)-(phenylmethyl)-2-oxazolidinone

Base Information

• Chemical Name: 3-<4-(1,3-dioxolan-2-yl)-1-oxo-3(R)-phenylbutyl>-4(S)-(phenylmethyl)-2-oxazolidinone
• CAS No.: 138571-30-9
• Molecular Formula: C₂₃H₂₅NO₅
• Molecular Weight: 395.455
• Mol file: 138571-30-9.mol

Synonyms:3-<4-(1,3-dioxolan-2-yl)-1-oxo-3(R)-phenylbutyl>-4(S)-(phenylmethyl)-2-oxazolidinone

Chemical Property of 3-<4-(1,3-dioxolan-2-yl)-1-oxo-3(R)-phenylbutyl>-4(S)-(phenylmethyl)-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-<4-(1,3-dioxolan-2-yl)-1-oxo-3(R)-phenylbutyl>-4(S)-(phenylmethyl)-2-oxazolidinone

There total 8 articles about 3-<4-(1,3-dioxolan-2-yl)-1-oxo-3(R)-phenylbutyl>-4(S)-(phenylmethyl)-2-oxazolidinone 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:

3-phenylglutaric acid anhydride (4160-80-9) → 3-<4-(1,3-dioxolan-2-yl)-1-oxo-3(R)-phenylbutyl>-4(S)-(phenylmethyl)-2-oxazolidinone (138571-30-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 86 percent / NaBH₄ / tetrahydrofuran / a) 0 deg C, 1 h, b) RT, 0.5 h

2: 100 percent / 2.5 M aq. NaOH

3: 57 percent / hexamethylphosphoric acid triamide; ethanol / Ambient temperature

4: 1.) oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, DMSO, -78 deg C, 0.5 h, 2.) CH₂Cl₂, DMSO, from -78 deg C to RT

5: TsOH / benzene / 2 h / 120 °C

6: 93 percent / 1 M aq. NaOH / tetrahydrofuran / 10 h / Heating

7: 1.) pivaloyl chloride, Et₃N / 1.) THF, -78 deg C, 2.) from -78 deg C to 0 deg C, 40 min

With sodium hydroxide; sodium tetrahydroborate; oxalyl dichloride; pivaloyl chloride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; benzene;

DOI:10.1021/jm00083a006

Reference yield:

4-phenyltetrahydropyran-2-one (61198-49-0,61949-75-5,71302-21-1,25547-53-9) → 3-<4-(1,3-dioxolan-2-yl)-1-oxo-3(R)-phenylbutyl>-4(S)-(phenylmethyl)-2-oxazolidinone (138571-30-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / 2.5 M aq. NaOH

2: 57 percent / hexamethylphosphoric acid triamide; ethanol / Ambient temperature

3: 1.) oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, DMSO, -78 deg C, 0.5 h, 2.) CH₂Cl₂, DMSO, from -78 deg C to RT

4: TsOH / benzene / 2 h / 120 °C

5: 93 percent / 1 M aq. NaOH / tetrahydrofuran / 10 h / Heating

6: 1.) pivaloyl chloride, Et₃N / 1.) THF, -78 deg C, 2.) from -78 deg C to 0 deg C, 40 min

With sodium hydroxide; oxalyl dichloride; pivaloyl chloride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; benzene;

DOI:10.1021/jm00083a006

Reference yield:

3-phenylglutaric acid (4165-96-2) → 3-<4-(1,3-dioxolan-2-yl)-1-oxo-3(R)-phenylbutyl>-4(S)-(phenylmethyl)-2-oxazolidinone (138571-30-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 95 percent / dicyclohexylcarbodiimide / CH₂Cl₂ / 0 °C

2: 86 percent / NaBH₄ / tetrahydrofuran / a) 0 deg C, 1 h, b) RT, 0.5 h

3: 100 percent / 2.5 M aq. NaOH

4: 57 percent / hexamethylphosphoric acid triamide; ethanol / Ambient temperature

5: 1.) oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, DMSO, -78 deg C, 0.5 h, 2.) CH₂Cl₂, DMSO, from -78 deg C to RT

6: TsOH / benzene / 2 h / 120 °C

7: 93 percent / 1 M aq. NaOH / tetrahydrofuran / 10 h / Heating

8: 1.) pivaloyl chloride, Et₃N / 1.) THF, -78 deg C, 2.) from -78 deg C to 0 deg C, 40 min

With sodium hydroxide; sodium tetrahydroborate; oxalyl dichloride; pivaloyl chloride; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; benzene;

DOI:10.1021/jm00083a006

upstream raw materials:

4-(1,3-dioxolan-2-yl)-3-phenylbutanoic acid

(S)-4-benzyl-2-oxazolidinone lithium salt

4-phenyltetrahydropyran-2-one

3-phenylglutaric acid anhydride

Downstream raw materials:

3-<4-(1,3-dioxolan-2-yl)-1-oxo-3(S)-phenyl-2(S)-azidobutyl>-4(S)-(phenylmethyl)-2-oxazolidinone

3(S)-<(tert-butyloxycarbonyl)amino>-α(S)-butyl-N-<4(S)-<(butylamino)carbonyl>-1(S)-(cyclohexylmethyl)-2(S)-hydroxy-5-methylhexyl>-2-oxo-4(S)-phenyl-1-piperidineacetamide

3(S)-azido-α(S)-butyl-2-oxo-4(S)-phenyl-1-piperidineacetic acid tert-butyl ester

3-<2(S)-azido-1,5-dioxo-3(S)-phenylpentyl>-4(S)-phenylmethyl-2-oxazolidinone