N²-(tert-butyloxycarbonyl)-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one

Base Information

• Chemical Name: N²-(tert-butyloxycarbonyl)-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one
• CAS No.: 128300-13-0
• Molecular Formula: C₁₈H₁₉NO₃
• Molecular Weight: 297.354
• Mol file: 128300-13-0.mol

Synonyms:N²-(tert-butyloxycarbonyl)-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one

Chemical Property of N²-(tert-butyloxycarbonyl)-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one

Chemical Property:

Purity/Quality:

95%+ or 98%+ ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N²-(tert-butyloxycarbonyl)-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one

There total 1 articles about N²-(tert-butyloxycarbonyl)-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one 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: 78.0%

tert-butyl (1S)-1-(chloromethyl)-5-hydroxy-1,2-dihydro-3H-benzo[e]indole-3-carboxylate (122745-41-9,130008-89-8,130007-86-2) + benzyl bromide (100-39-0) → N2-(tert-butyloxycarbonyl)-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (128300-13-0) + 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(chloromethyl)-1,2-dihydro-3H-benzindole (128300-11-8)

Guidance literature:

With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1016/j.bmc.2016.09.068

Reference yield: 51.0%

5-[3-(4-fluorophenyl)ureido]benzo[b]selenophene-2-carboxylic acid (1429048-08-7) + N2-(tert-butyloxycarbonyl)-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (128300-13-0) → (S)-1-(2-(1-(chloromethyl)-5-hydroxy-2,3-dihydro-1H-benzo[e]indole-3-carbonyl)benzo[b]selenophen-5-yl)-3-(4-fluorophenyl)urea (1429047-96-0)

Guidance literature:

N²-(tert-butyloxycarbonyl)-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one; With hydrogenchloride; In ethyl acetate; at -78 - 20 ℃; for 1.5h;

5-[3-(4-fluorophenyl)ureido]benzo[b]selenophene-2-carboxylic acid; With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 8.75h;

DOI:10.1039/c6ob02729f

Reference yield:

N2-(tert-butyloxycarbonyl)-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (128300-13-0) → Cbz-Val-Cit-PAMA-(alloc-PEG3-amide)-Pro-CBI

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogenchloride / ethyl acetate / 1.5 h / -78 - 23 °C / Inert atmosphere

2.1: triethylamine / water; tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

3.1: acetonitrile / 2 h / 20 °C / Molecular sieve; Inert atmosphere

3.2: 6 h / -10 - 20 °C

With hydrogenchloride; triethylamine; acetonitrile; In tetrahydrofuran; water; ethyl acetate;

upstream raw materials:

tert-butyl (1S)-1-(chloromethyl)-5-hydroxy-1,2-dihydro-3H-benzo[e]indole-3-carboxylate

benzyl bromide

Downstream raw materials:

tert-butyl (1S)-1-(chloromethyl)-5-hydroxy-1,2-dihydro-3H-benzo[e]indole-3-carboxylate

(S)-1-(2-(1-(chloromethyl)-5-hydroxy-2,3-dihydro-1H-benzo[e]indole-3-carbonyl)benzo[b]selenophen-5-yl)-3-(4-fluorophenyl)urea