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

Base Information

Chemical Name:3-(4-hydroxymethyl-2-phenyl-4,5-dihydro-oxazol-5-yl)-N-methoxy-N-methyl-propionamide
CAS No.:503560-12-1
Molecular Formula:C₁₅H₂₀N₂O₄
Molecular Weight:292.335
Hs Code.:

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

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

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

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

There total 10 articles about 3-(4-hydroxymethyl-2-phenyl-4,5-dihydro-oxazol-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: 94.0%

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

: 503560-12-1
3-(4-hydroxymethyl-2-phenyl-4,5-dihydro-oxazol-5-yl)-N-methoxy-N-methyl-propionamide

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1016/S0957-4166(02)00794-2

Reference yield:

: 208935-32-4
(4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazoline

: 503560-12-1
3-(4-hydroxymethyl-2-phenyl-4,5-dihydro-oxazol-5-yl)-N-methoxy-N-methyl-propionamide

Guidance literature:: Multi-step reaction with 6 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

6.1: 94 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

With lithium hydroxide; tetrabutyl ammonium fluoride; 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:

: 482315-18-4
N-[(1S)-2-hydroxy-1-(tert-butyldimethylsilanyloxymethyl)-3-butenyl]-benzamide

: 503560-12-1
3-(4-hydroxymethyl-2-phenyl-4,5-dihydro-oxazol-5-yl)-N-methoxy-N-methyl-propionamide

Guidance literature:: Multi-step reaction with 8 steps

1.1: 99 percent / pyridine / CH₂Cl₂ / 12 h

2.1: 75 percent / K₂CO₃; Pd(PPh₃)4 / acetonitrile / 24 h / Heating

3.1: O₃ / methanol / -78 °C

4.1: LiCl; DBU / acetonitrile / 1 h

4.2: 2.03 g / acetonitrile / 2 h

5.1: 82.4 percent / CuBr; Red-Al; 2-butanol / tetrahydrofuran / 4 h / -20 °C

6.1: aq. LiOH / tetrahydrofuran / 2 h

7.1: 491 mg / Et₃N; DCC; HOBt / CH₂Cl₂ / 12 h

8.1: 94 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

With pyridine; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; 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