(3S)-[1-(2-azidobenzoyl)]-3,4-dihydro-4-methyl-3-phenylmethyl-[1,4]benzodiazepin-2,5(1H)-dione

Base Information

Chemical Name:(3S)-[1-(2-azidobenzoyl)]-3,4-dihydro-4-methyl-3-phenylmethyl-[1,4]benzodiazepin-2,5(1H)-dione
CAS No.:196928-08-2
Molecular Formula:C₂₄H₁₉N₅O₃
Molecular Weight:425.447
Hs Code.:

Synonyms:(3S)-[1-(2-azidobenzoyl)]-3,4-dihydro-4-methyl-3-phenylmethyl-[1,4]benzodiazepin-2,5(1H)-dione

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Chemical Property of (3S)-[1-(2-azidobenzoyl)]-3,4-dihydro-4-methyl-3-phenylmethyl-[1,4]benzodiazepin-2,5(1H)-dione

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Technology Process of (3S)-[1-(2-azidobenzoyl)]-3,4-dihydro-4-methyl-3-phenylmethyl-[1,4]benzodiazepin-2,5(1H)-dione

There total 7 articles about (3S)-[1-(2-azidobenzoyl)]-3,4-dihydro-4-methyl-3-phenylmethyl-[1,4]benzodiazepin-2,5(1H)-dione 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: 82.0%

: 34897-85-3
o-azidobenzoyl chloride

: 50886-63-0
(3S)-3,4-dihydro-4-methyl-3-phenylmethyl-[1,4]benzodiazepin-2,5(1H)-dione

: 196928-08-2
(3S)-[1-(2-azidobenzoyl)]-3,4-dihydro-4-methyl-3-phenylmethyl-[1,4]benzodiazepin-2,5(1H)-dione

Guidance literature:: With potassium hexamethylsilazane; 1.) THF, -78 deg C, 1 h; 2.) THF, -78 deg C, 30 min, then room temp., 1 h;
DOI:10.1246/cl.1997.869

Reference yield:

: 34897-85-3
o-azidobenzoyl chloride

: 196928-08-2
(3S)-[1-(2-azidobenzoyl)]-3,4-dihydro-4-methyl-3-phenylmethyl-[1,4]benzodiazepin-2,5(1H)-dione

Guidance literature:: Multi-step reaction with 4 steps

1.1: 94 percent / Et₃N / tetrahydrofuran / 16 h / 0 - 20 °C

2.1: n-Bu₃P / toluene / 7.5 h / 20 °C / Heating

3.1: 87 percent / CF₃COOH / H₂O; tetrahydrofuran / 7 h / 20 °C

4.1: KHDMS / tetrahydrofuran / 1 h / -78 °C

4.2: 82 percent / tetrahydrofuran / 1.5 h / -78 - 20 °C

With tributylphosphine; potassium hexamethylsilazane; triethylamine; trifluoroacetic acid; In tetrahydrofuran; water; toluene; 1.1: Acylation / 2.1: Cyclization / 3.1: Hydrolysis / 4.1: Metallation / 4.2: Acylation;
DOI:10.1016/S0040-4020(98)00437-2

Reference yield:

: 31162-13-7
2-azidobenzoic acid

: 196928-08-2
(3S)-[1-(2-azidobenzoyl)]-3,4-dihydro-4-methyl-3-phenylmethyl-[1,4]benzodiazepin-2,5(1H)-dione

Guidance literature:: Multi-step reaction with 5 steps

1.1: SOCl₂ / tetrahydrofuran / 2 h / 80 °C

2.1: 94 percent / Et₃N / tetrahydrofuran / 16 h / 0 - 20 °C

3.1: n-Bu₃P / toluene / 7.5 h / 20 °C / Heating

4.1: 87 percent / CF₃COOH / H₂O; tetrahydrofuran / 7 h / 20 °C

5.1: KHDMS / tetrahydrofuran / 1 h / -78 °C

5.2: 82 percent / tetrahydrofuran / 1.5 h / -78 - 20 °C

With thionyl chloride; tributylphosphine; potassium hexamethylsilazane; triethylamine; trifluoroacetic acid; In tetrahydrofuran; water; toluene; 1.1: Substitution / 2.1: Acylation / 3.1: Cyclization / 4.1: Hydrolysis / 5.1: Metallation / 5.2: Acylation;
DOI:10.1016/S0040-4020(98)00437-2