2(S)-(2-bromo-2-propenyl)-4-[(cyclohexylmethyl)[2-[methyl[2-(2-pyridinyl)ethyl]amino]-2-oxo-ethyl]amino]-4-oxobutanoic acid

Base Information

Chemical Name:2(S)-(2-bromo-2-propenyl)-4-[(cyclohexylmethyl)[2-[methyl[2-(2-pyridinyl)ethyl]amino]-2-oxo-ethyl]amino]-4-oxobutanoic acid
CAS No.:294856-58-9
Molecular Formula:C₂₄H₃₄BrN₃O₄
Molecular Weight:508.456
Hs Code.:

Synonyms:2(S)-(2-bromo-2-propenyl)-4-[(cyclohexylmethyl)[2-[methyl[2-(2-pyridinyl)ethyl]amino]-2-oxo-ethyl]amino]-4-oxobutanoic acid

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Chemical Property of 2(S)-(2-bromo-2-propenyl)-4-[(cyclohexylmethyl)[2-[methyl[2-(2-pyridinyl)ethyl]amino]-2-oxo-ethyl]amino]-4-oxobutanoic acid

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Technology Process of 2(S)-(2-bromo-2-propenyl)-4-[(cyclohexylmethyl)[2-[methyl[2-(2-pyridinyl)ethyl]amino]-2-oxo-ethyl]amino]-4-oxobutanoic acid

There total 15 articles about 2(S)-(2-bromo-2-propenyl)-4-[(cyclohexylmethyl)[2-[methyl[2-(2-pyridinyl)ethyl]amino]-2-oxo-ethyl]amino]-4-oxobutanoic acid 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: 77.0%

: 294856-57-8
3-[4-bromo-2(S)-[2-[(cyclohexylmethyl)[2-[methyl[2-(2-pyridinyl)ethyl]amino]-2-oxoethyl]amino]-2-oxoethyl]-1-oxo-4-pentenyl]-4(S)-(1-methylethyl)-2-oxazolidinone

: 294856-58-9
2(S)-(2-bromo-2-propenyl)-4-[(cyclohexylmethyl)[2-[methyl[2-(2-pyridinyl)ethyl]amino]-2-oxo-ethyl]amino]-4-oxobutanoic acid

Guidance literature:: With lithium hydroperoxide; In tetrahydrofuran; at 0 ℃; for 0.666667h;
DOI:10.1139/v99-233

Reference yield:

: 86953-48-2
4-bromo-pent-4-enoic acid

: 294856-58-9
2(S)-(2-bromo-2-propenyl)-4-[(cyclohexylmethyl)[2-[methyl[2-(2-pyridinyl)ethyl]amino]-2-oxo-ethyl]amino]-4-oxobutanoic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: 99 percent / (COCl)2; DMF / CH₂Cl₂ / 18 h / 20 °C

2.1: n-BuLi; Ph₃CH / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: 98 percent / tetrahydrofuran / 2.5 h / 20 °C

3.1: NaHMDS / tetrahydrofuran / 1.5 h / -78 °C

3.2: 53 percent / tetrahydrofuran / 1.5 h / -78 °C

4.1: 100 percent / 4 N aq. HCl / dioxane / 20 h / 25 °C

5.1: Et₃N / tetrahydrofuran / 0.5 h / -40 °C

6.1: 100 percent / tetrahydrofuran / 2.5 h / 25 °C

7.1: 77 percent / aq. LiOOH / tetrahydrofuran / 0.67 h / 0 °C

With hydrogenchloride; n-butyllithium; oxalyl dichloride; lithium hydroperoxide; triphenylmethane; sodium hexamethyldisilazane; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; 1.1: Chlorination / 2.1: Metallation / 2.2: Substitution / 3.1: Metallation / 3.2: Condensation / 4.1: Hydrolysis / 5.1: Substitution / 6.1: Substitution / 7.1: Ring cleavage;
DOI:10.1139/v99-233

Reference yield:

: 92975-38-7
4-bromo-4-pentenoic acid tert-butyl ester

: 294856-58-9
2(S)-(2-bromo-2-propenyl)-4-[(cyclohexylmethyl)[2-[methyl[2-(2-pyridinyl)ethyl]amino]-2-oxo-ethyl]amino]-4-oxobutanoic acid

Guidance literature:: Multi-step reaction with 8 steps

1.1: 86 percent / TFA / CH₂Cl₂ / 48 h / 25 °C

2.1: 99 percent / (COCl)2; DMF / CH₂Cl₂ / 18 h / 20 °C

3.1: n-BuLi; Ph₃CH / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: 98 percent / tetrahydrofuran / 2.5 h / 20 °C

4.1: NaHMDS / tetrahydrofuran / 1.5 h / -78 °C

4.2: 53 percent / tetrahydrofuran / 1.5 h / -78 °C

5.1: 100 percent / 4 N aq. HCl / dioxane / 20 h / 25 °C

6.1: Et₃N / tetrahydrofuran / 0.5 h / -40 °C

7.1: 100 percent / tetrahydrofuran / 2.5 h / 25 °C

8.1: 77 percent / aq. LiOOH / tetrahydrofuran / 0.67 h / 0 °C

With hydrogenchloride; n-butyllithium; oxalyl dichloride; lithium hydroperoxide; triphenylmethane; sodium hexamethyldisilazane; triethylamine; N,N-dimethyl-formamide; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; 1.1: Hydrolysis / 2.1: Chlorination / 3.1: Metallation / 3.2: Substitution / 4.1: Metallation / 4.2: Condensation / 5.1: Hydrolysis / 6.1: Substitution / 7.1: Substitution / 8.1: Ring cleavage;
DOI:10.1139/v99-233