3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-N-(4-((tert-butoxycarbonyl)aminomethyl)phenyl)propanamide

Base Information

Chemical Name:3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-N-(4-((tert-butoxycarbonyl)aminomethyl)phenyl)propanamide
CAS No.:1268335-80-3
Molecular Formula:C₂₂H₂₇BN₂O₅
Molecular Weight:410.278
Hs Code.:

Synonyms:3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-N-(4-((tert-butoxycarbonyl)aminomethyl)phenyl)propanamide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-N-(4-((tert-butoxycarbonyl)aminomethyl)phenyl)propanamide

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of 3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-N-(4-((tert-butoxycarbonyl)aminomethyl)phenyl)propanamide

There total 15 articles about 3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-N-(4-((tert-butoxycarbonyl)aminomethyl)phenyl)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: 84.9%

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

: 94838-55-8
tert-butyl (4-aminobenzyl)carbamate

: 1268335-80-3
3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-N-(4-((tert-butoxycarbonyl)aminomethyl)phenyl)propanamide

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

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 4403-71-8
(4-aminomethyl)aniline

: 1268335-80-3
3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-N-(4-((tert-butoxycarbonyl)aminomethyl)phenyl)propanamide

Guidance literature:: Multi-step reaction with 2 steps

1: potassium carbonate / tetrahydrofuran / 20 °C

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C

With potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/acs.jmedchem.9b00736

Reference yield:

: 22433-91-6
2-bromoisophthalic acid

: 1268335-80-3
3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-N-(4-((tert-butoxycarbonyl)aminomethyl)phenyl)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;