3-[(E)-4-(acetylamino)cinnamoyl]-5-(tert-butyloxycarbonylamino)-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indole

Base Information

Chemical Name:3-[(E)-4-(acetylamino)cinnamoyl]-5-(tert-butyloxycarbonylamino)-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indole
CAS No.:204915-93-5
Molecular Formula:C₂₉H₃₀ClN₃O₄
Molecular Weight:520.028
Hs Code.:

Synonyms:3-[(E)-4-(acetylamino)cinnamoyl]-5-(tert-butyloxycarbonylamino)-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indole

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Chemical Property of 3-[(E)-4-(acetylamino)cinnamoyl]-5-(tert-butyloxycarbonylamino)-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indole

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Technology Process of 3-[(E)-4-(acetylamino)cinnamoyl]-5-(tert-butyloxycarbonylamino)-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indole

There total 7 articles about 3-[(E)-4-(acetylamino)cinnamoyl]-5-(tert-butyloxycarbonylamino)-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indole 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:

: 193225-64-8
3-(tert-butyloxycarbonyl)-1-(chloromethyl)-5-nitro-1,2-dihydro-3H-benzindole

: 204915-93-5
3-[(E)-4-(acetylamino)cinnamoyl]-5-(tert-butyloxycarbonylamino)-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indole

Guidance literature:: Multi-step reaction with 6 steps

1: HCl / dioxane / 2 h / 20 °C

2: 81 percent / pyridine / 0.17 h / 20 °C

3: 89 percent / H₂ / PtO₂ / benzene / 1 h / 50 °C

4: 74 percent / dioxane / 8 h / 70 °C

5: aq. Cs₂CO₃ / 1-methyl-pyrrolidin-2-one / 0.75 h / 20 °C

6: 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide*HCl; DMA; DMA*HCl / 0.5 h / 20 °C

With pyridine; hydrogenchloride; DMA*HCl; hydrogen; 2,4-dichlorophenoxyacetic acid dimethylamine; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; platinum(IV) oxide; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; benzene; 1: acidolysis / 2: Acylation / 3: Reduction / 4: Acylation / 5: Hydrolysis / 6: Condensation;
DOI:10.1021/jm990136b

Reference yield:

: 204915-90-2
1-(chloromethyl)-5-nitro-3-(trifluoroacetyl)-1,2-dihydro-3H-benz[e]indole

: 204915-93-5
3-[(E)-4-(acetylamino)cinnamoyl]-5-(tert-butyloxycarbonylamino)-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indole

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / H₂ / PtO₂ / benzene / 1 h / 50 °C

2: 74 percent / dioxane / 8 h / 70 °C

3: aq. Cs₂CO₃ / 1-methyl-pyrrolidin-2-one / 0.75 h / 20 °C

4: 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide*HCl; DMA; DMA*HCl / 0.5 h / 20 °C

With DMA*HCl; hydrogen; 2,4-dichlorophenoxyacetic acid dimethylamine; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; platinum(IV) oxide; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; benzene; 1: Reduction / 2: Acylation / 3: Hydrolysis / 4: Condensation;
DOI:10.1021/jm990136b

Reference yield:

: 1-(chloromethyl)-5-nitro-1,2-dihydro-3H-benz[e]indole hydrochloride

: 204915-93-5
3-[(E)-4-(acetylamino)cinnamoyl]-5-(tert-butyloxycarbonylamino)-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indole

Guidance literature:: Multi-step reaction with 5 steps

1: 81 percent / pyridine / 0.17 h / 20 °C

2: 89 percent / H₂ / PtO₂ / benzene / 1 h / 50 °C

3: 74 percent / dioxane / 8 h / 70 °C

4: aq. Cs₂CO₃ / 1-methyl-pyrrolidin-2-one / 0.75 h / 20 °C

5: 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide*HCl; DMA; DMA*HCl / 0.5 h / 20 °C

With pyridine; DMA*HCl; hydrogen; 2,4-dichlorophenoxyacetic acid dimethylamine; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; platinum(IV) oxide; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; benzene; 1: Acylation / 2: Reduction / 3: Acylation / 4: Hydrolysis / 5: Condensation;
DOI:10.1021/jm990136b