3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-N-(4-methoxylphenyl)propanamide

Base Information

Chemical Name:3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-N-(4-methoxylphenyl)propanamide
CAS No.:1268335-79-0
Molecular Formula:C₁₇H₁₈BNO₄
Molecular Weight:311.145
Hs Code.:

Synonyms:3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-N-(4-methoxylphenyl)propanamide

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Chemical Property of 3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-N-(4-methoxylphenyl)propanamide

Chemical Property:

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Technology Process of 3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-N-(4-methoxylphenyl)propanamide

There total 14 articles about 3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-N-(4-methoxylphenyl)propanamide 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: 40.5%

: 1268335-33-6
3-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-7-yl)propanoic acid

: 104-94-9
4-methoxy-aniline

: 1268335-79-0
3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-N-(4-methoxylphenyl)propanamide

Guidance literature:: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃;
DOI:10.1021/acs.jmedchem.9b00736

Reference yield:

: 22433-91-6
2-bromoisophthalic acid

: 1268335-79-0
3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-N-(4-methoxylphenyl)propanamide

Guidance literature:: Multi-step reaction with 11 steps

1.1: thionyl chloride / 9 h / 100 °C

1.2: 2 h / 20 - 25 °C

2.1: lithium borohydride / diethyl ether; tetrahydrofuran / 20 - 25 °C

2.2: pH 6 - 7

3.1: silica gel; pyridinium chlorochromate / dichloromethane / 20 - 25 °C

4.1: toluene-4-sulfonic acid / toluene / Reflux

4.2: 2 h / Reflux

5.1: sodium tetrahydroborate / methanol / 1 h / 20 - 25 °C

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 7 h / 20 - 25 °C

7.1: n-butyllithium / hexane; tetrahydrofuran / 0.33 h / -78 °C

7.2: -78 - 25 °C

8.1: sodium hydride / tetrahydrofuran; mineral oil / 20 h / 20 - 25 °C

9.1: hydrogen / platinum(IV) oxide trihydrate / methanol / 20 - 25 °C

10.1: sodium hydroxide; water / methanol / 1 h / Reflux

10.2: pH 2 / Acidic conditions

11.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 - 25 °C

With sodium tetrahydroborate; lithium borohydride; n-butyllithium; thionyl chloride; water; hydrogen; silica gel; sodium hydride; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; sodium hydroxide; platinum(IV) oxide trihydrate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; mineral oil;

Reference yield:

: 576-22-7
2-Bromo-m-xylene

: 1268335-79-0
3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-N-(4-methoxylphenyl)propanamide

Guidance literature:: Multi-step reaction with 12 steps

1.1: water; potassium permanganate / tert-butyl alcohol / 12 h / 70 °C

2.1: thionyl chloride / 9 h / 100 °C

2.2: 2 h / 20 - 25 °C

3.1: lithium borohydride / diethyl ether; tetrahydrofuran / 20 - 25 °C

3.2: pH 6 - 7

4.1: silica gel; pyridinium chlorochromate / dichloromethane / 20 - 25 °C

5.1: toluene-4-sulfonic acid / toluene / Reflux

5.2: 2 h / Reflux

6.1: sodium tetrahydroborate / methanol / 1 h / 20 - 25 °C

7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 7 h / 20 - 25 °C

8.1: n-butyllithium / hexane; tetrahydrofuran / 0.33 h / -78 °C

8.2: -78 - 25 °C

9.1: sodium hydride / tetrahydrofuran; mineral oil / 20 h / 20 - 25 °C

10.1: hydrogen / platinum(IV) oxide trihydrate / methanol / 20 - 25 °C

11.1: sodium hydroxide; water / methanol / 1 h / Reflux

11.2: pH 2 / Acidic conditions

12.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 - 25 °C

With sodium tetrahydroborate; potassium permanganate; lithium borohydride; n-butyllithium; thionyl chloride; water; hydrogen; silica gel; sodium hydride; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; sodium hydroxide; platinum(IV) oxide trihydrate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; mineral oil; tert-butyl alcohol;