(S)-9-[(S)-1-(2-Azido-benzoyl)-2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-3-ylmethyl]-2-isobutyl-3-oxo-2,3-dihydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (S)-9-[(S)-1-(2-Azido-benzoyl)-2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-3-ylmethyl]-2-isobutyl-3-oxo-2,3-dihydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester
• CAS No.: 210702-48-0
• Molecular Formula: C₃₉H₃₃N₇O₆
• Molecular Weight: 695.734

Synonyms:(S)-9-[(S)-1-(2-Azido-benzoyl)-2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-3-ylmethyl]-2-isobutyl-3-oxo-2,3-dihydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester

Chemical Property of (S)-9-[(S)-1-(2-Azido-benzoyl)-2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-3-ylmethyl]-2-isobutyl-3-oxo-2,3-dihydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (S)-9-[(S)-1-(2-Azido-benzoyl)-2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-3-ylmethyl]-2-isobutyl-3-oxo-2,3-dihydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester

There total 11 articles about (S)-9-[(S)-1-(2-Azido-benzoyl)-2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-3-ylmethyl]-2-isobutyl-3-oxo-2,3-dihydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester 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%

o-azidobenzoyl chloride (34897-85-3) + (S)-9-((S)-2,5-Dioxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-3-ylmethyl)-2-isobutyl-3-oxo-2,3-dihydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester (210702-47-9) → (S)-9-[(S)-1-(2-Azido-benzoyl)-2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-3-ylmethyl]-2-isobutyl-3-oxo-2,3-dihydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester (210702-48-0)

Guidance literature:

With dmap; triethylamine;

DOI:10.1021/ja9809408

Reference yield:

Z-Leu-OH (2018-66-8) → (S)-9-[(S)-1-(2-Azido-benzoyl)-2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-3-ylmethyl]-2-isobutyl-3-oxo-2,3-dihydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester (210702-48-0)

Guidance literature:

Multi-step reaction with 8 steps

1: DCC

2: DDQ / toluene / Heating

3: 1.) Hg(OTFA)2, 2.) KI, 3.) I₂

4: Pd₂(dba)3, P(o-tolyl)3, K₂CO₃ / toluene / Heating

5: Zn, AcOH

6: DCC

7: 93 percent / Zn, AcOH / ethyl acetate

8: 82 percent / Et₃N, DMAP

With dmap; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; iodine; mercury(II) trifluoroacetate; potassium carbonate; acetic acid; triethylamine; dicyclohexyl-carbodiimide; tris-(o-tolyl)phosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium iodide; zinc; In ethyl acetate; toluene;

DOI:10.1021/ja9809408

Reference yield:

Troc-Trp-OH (88050-14-0) → (S)-9-[(S)-1-(2-Azido-benzoyl)-2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-3-ylmethyl]-2-isobutyl-3-oxo-2,3-dihydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester (210702-48-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 88 percent / DCC, DMAP

2: 81 percent / BH₃*THF, TFA

3: DCC

4: DDQ / toluene / Heating

5: 1.) Hg(OTFA)2, 2.) KI, 3.) I₂

6: Pd₂(dba)3, P(o-tolyl)3, K₂CO₃ / toluene / Heating

7: Zn, AcOH

8: DCC

9: 93 percent / Zn, AcOH / ethyl acetate

10: 82 percent / Et₃N, DMAP

With dmap; borane-THF; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; iodine; mercury(II) trifluoroacetate; potassium carbonate; acetic acid; triethylamine; dicyclohexyl-carbodiimide; tris-(o-tolyl)phosphine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium iodide; zinc; In ethyl acetate; toluene;

DOI:10.1021/ja9809408

upstream raw materials:

o-azidobenzoyl chloride

(S)-9-((S)-2,5-Dioxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-3-ylmethyl)-2-isobutyl-3-oxo-2,3-dihydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester

Z-Leu-OH

Troc-Trp-OH

Downstream raw materials:

(S)-9-((S)-5,13-Dioxo-5,6,7,13-tetrahydro-6,8,13a-triaza-benzo[3,4]cyclohepta[1,2-b]naphthalen-7-ylmethyl)-2-isobutyl-3-oxo-2,3-dihydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester

Asperlicin

phenylmethyl 2,3,9,9a-tetrahydro-9-hydroxy-2-(2-methylpropyl)-3-oxo-9-[(5,6,7,13-tetrahydro-5,13-dioxoquinazolino[3,2-a][1,4]benzodiazepin-7-yl)methyl]-1H-imidazo[1,2-a]indole-1-carboxylic acid ester

(S)-9-((7S,7aS)-5,13-Dioxo-5,6,7,7a,8,13-hexahydro-6,8,13a-triaza-benzo[3,4]cyclohepta[1,2-b]naphthalen-7-ylmethyl)-9-hydroxy-2-isobutyl-9a-methoxy-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester

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