(1-{[(4-amino-benzyl)-methyl-carbamoyl]-methyl}-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetic acid tert-butyl ester

Base Information

Chemical Name:(1-{[(4-amino-benzyl)-methyl-carbamoyl]-methyl}-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetic acid tert-butyl ester
CAS No.:380396-44-1
Molecular Formula:C₂₆H₃₃N₃O₄
Molecular Weight:451.566
Hs Code.:

(1-{[(4-amino-benzyl)-methyl-carbamoyl]-methyl}-2-oxo-2,3,4,5-tetrahydro-1<i>H</i>-benzo[<i>b</i>]azepin-5-yl)-acetic acid <i>tert</i>-butyl ester

Synonyms:(1-{[(4-amino-benzyl)-methyl-carbamoyl]-methyl}-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetic acid tert-butyl ester

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Chemical Property of (1-{[(4-amino-benzyl)-methyl-carbamoyl]-methyl}-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetic acid tert-butyl ester

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Technology Process of (1-{[(4-amino-benzyl)-methyl-carbamoyl]-methyl}-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetic acid tert-butyl ester

There total 13 articles about (1-{[(4-amino-benzyl)-methyl-carbamoyl]-methyl}-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetic acid tert-butyl 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: 99.0%

: 380396-43-0
(1-{[methyl-(4-nitro-benzyl)-carbamoyl]-methyl}-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetic acid tert-butyl ester

: 380396-44-1
(1-{[(4-amino-benzyl)-methyl-carbamoyl]-methyl}-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetic acid tert-butyl ester

Guidance literature:: With iron(III) chloride; pyrographite; hydrazine hydrate; In methanol; at 60 ℃; for 1h;
DOI:10.1016/S0968-0896(02)00616-8

Reference yield:

: 5202-89-1
4-chlorobenzenesulfonyl chloride

: 380396-44-1
(1-{[(4-amino-benzyl)-methyl-carbamoyl]-methyl}-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 87 percent / pyridine / tetrahydrofuran / 2 h / 20 °C

2.1: NaH / dimethylsulfoxide-d6; tetrahydrofuran / 20 °C

2.2: 57 percent / H₂O / dimethylsulfoxide / 150 °C

3.1: NaH / dimethylformamide / 0 °C

3.2: 84.2 percent / dimethylformamide / 20 °C

4.1: H₂ / 5 percent Pt/C / ethanol; dioxane / 96 h / 20 °C / atmospheric pressure

5.1: NaH / dimethylformamide / 1 h / 10 - 20 °C

5.2: dimethylformamide / 12 h / 10 - 20 °C

6.1: 17.5 g / aq. NaOH / dioxane / 1 h / 20 °C

7.1: HATU; DIEA / dimethylformamide / 1 h / 10 °C

7.2: 71 percent / DIEA / CH₂Cl₂ / 13 h / 0 - 20 °C

8.1: 99 percent / FeCl₃*6H₂O; activated carbon; N₂H₄*H₂O / methanol / 1 h / 60 °C

With pyridine; sodium hydroxide; hydrogen; iron(III) chloride; sodium hydride; pyrographite; hydrazine hydrate; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; platinum on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dimethylsulfoxide-d6; ethanol; N,N-dimethyl-formamide; 2.1: Dieckmann condensation / 3.2: Wittig-Horner olefination;
DOI:10.1016/S0968-0896(02)00616-8

Reference yield:

: 16511-38-9
1H-[1]benzazepin-2,5(3H,4H)-dione

: 380396-44-1
(1-{[(4-amino-benzyl)-methyl-carbamoyl]-methyl}-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaH / dimethylformamide / 1 h / 0 °C

1.2: 90.5 percent / dimethylformamide / 72 h / 20 °C

2.1: 96 percent / H₂ / 10 percent Pd/C / ethanol; dioxane / 20 °C / atmospheric pressure

3.1: NaH / dimethylformamide / 1 h / 10 - 20 °C

3.2: dimethylformamide / 12 h / 10 - 20 °C

4.1: 17.5 g / aq. NaOH / dioxane / 1 h / 20 °C

5.1: HATU; DIEA / dimethylformamide / 1 h / 10 °C

5.2: 71 percent / DIEA / CH₂Cl₂ / 13 h / 0 - 20 °C

6.1: 99 percent / FeCl₃*6H₂O; activated carbon; N₂H₄*H₂O / methanol / 1 h / 60 °C

With sodium hydroxide; hydrogen; iron(III) chloride; sodium hydride; pyrographite; hydrazine hydrate; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; N,N-dimethyl-formamide; 1.2: Wittig-Horner olefination;
DOI:10.1016/S0968-0896(02)00616-8