3-((4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazol-5-yl)-N-methoxy-N-methyl-propionamide

Base Information

• Chemical Name: 3-((4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazol-5-yl)-N-methoxy-N-methyl-propionamide
• CAS No.: 503560-06-3
• Molecular Formula: C₂₁H₃₄N₂O₄Si
• Molecular Weight: 406.597

Synonyms:3-((4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazol-5-yl)-N-methoxy-N-methyl-propionamide

Chemical Property of 3-((4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazol-5-yl)-N-methoxy-N-methyl-propionamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-((4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazol-5-yl)-N-methoxy-N-methyl-propionamide

There total 9 articles about 3-((4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazol-5-yl)-N-methoxy-N-methyl-propionamide 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:

(4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazoline (208935-32-4) → 3-((4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazol-5-yl)-N-methoxy-N-methyl-propionamide (503560-06-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: O₃ / methanol / -78 °C

2.1: LiCl; DBU / acetonitrile / 1 h

2.2: 2.03 g / acetonitrile / 2 h

3.1: 82.4 percent / CuBr; Red-Al; 2-butanol / tetrahydrofuran / 4 h / -20 °C

4.1: aq. LiOH / tetrahydrofuran / 2 h

5.1: 491 mg / Et₃N; DCC; HOBt / CH₂Cl₂ / 12 h

With lithium hydroxide; benzotriazol-1-ol; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; sodium bis(2-methoxyethoxy)aluminium dihydride; iso-butanol; lithium chloride; copper(I) bromide; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1016/S0957-4166(02)00794-2

Reference yield:

N-[2-(tert-butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-benzamide (503560-10-9) → 3-((4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazol-5-yl)-N-methoxy-N-methyl-propionamide (503560-06-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 96 percent / tetrahydrofuran / 1 h / -78 °C

2.1: 99 percent / pyridine / CH₂Cl₂ / 12 h

3.1: 75 percent / K₂CO₃; Pd(PPh₃)4 / acetonitrile / 24 h / Heating

4.1: O₃ / methanol / -78 °C

5.1: LiCl; DBU / acetonitrile / 1 h

5.2: 2.03 g / acetonitrile / 2 h

6.1: 82.4 percent / CuBr; Red-Al; 2-butanol / tetrahydrofuran / 4 h / -20 °C

7.1: aq. LiOH / tetrahydrofuran / 2 h

8.1: 491 mg / Et₃N; DCC; HOBt / CH₂Cl₂ / 12 h

With pyridine; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; benzotriazol-1-ol; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; sodium bis(2-methoxyethoxy)aluminium dihydride; iso-butanol; lithium chloride; copper(I) bromide; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1016/S0957-4166(02)00794-2

Reference yield:

N-((1S)-2-acetoxy-1-(tert-butyldimethylsilanyloxymethyl)-3-butenyl)-benzamide (497227-95-9) → 3-((4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazol-5-yl)-N-methoxy-N-methyl-propionamide (503560-06-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 75 percent / K₂CO₃; Pd(PPh₃)4 / acetonitrile / 24 h / Heating

2.1: O₃ / methanol / -78 °C

3.1: LiCl; DBU / acetonitrile / 1 h

3.2: 2.03 g / acetonitrile / 2 h

4.1: 82.4 percent / CuBr; Red-Al; 2-butanol / tetrahydrofuran / 4 h / -20 °C

5.1: aq. LiOH / tetrahydrofuran / 2 h

6.1: 491 mg / Et₃N; DCC; HOBt / CH₂Cl₂ / 12 h

With lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; benzotriazol-1-ol; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; sodium bis(2-methoxyethoxy)aluminium dihydride; iso-butanol; lithium chloride; copper(I) bromide; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1016/S0957-4166(02)00794-2

upstream raw materials:

N,O-dimethylhydroxylamine*hydrochloride

3-[(4S,5S)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-2-phenyl-4,5-dihydro-oxazol-5-yl]-propionic acid

(4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazoline

N-[2-(tert-butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-benzamide

Downstream raw materials:

3-((4S,trans)-4,5-dihydro-4-methyl-2-phenyloxazol-5-yl)-heptadecan-3-one-16-ethylenacetal

3-(4-iodomethyl-2-phenyl-4,5-dihydro-oxazol-5-yl)-N-methoxy-N-methyl-propionamide

3-((4S,trans)-4,5-dihydro-4-methyl-2-phenyloxazol-5-yl)-N-methoxy-N-methyl propionamide

3-(4-hydroxymethyl-2-phenyl-4,5-dihydro-oxazol-5-yl)-N-methoxy-N-methyl-propionamide

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