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

Base Information

• Chemical Name: 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
• CAS No.: 294856-57-8
• Molecular Formula: C₃₀H₄₃BrN₄O₅
• Molecular Weight: 619.599

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of 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

There total 13 articles about 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 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: 100.0%

2-<(cyclohexylmethyl)amino>-N-methyl-N-<2-(2-pyridinyl)ethyl>acetamide (192516-54-4) + C18H26BrNO6 → 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 (294856-57-8)

Guidance literature:

In tetrahydrofuran; at 25 ℃; for 2.5h;

DOI:10.1139/v99-233

Reference yield:

4-bromo-pent-4-enoic acid (86953-48-2) → 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 (294856-57-8)

Guidance literature:

Multi-step reaction with 6 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

With hydrogenchloride; n-butyllithium; oxalyl dichloride; 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;

DOI:10.1139/v99-233

Reference yield:

4-bromo-4-pentenoic acid tert-butyl ester (92975-38-7) → 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 (294856-57-8)

Guidance literature:

Multi-step reaction with 7 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

With hydrogenchloride; n-butyllithium; oxalyl dichloride; 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;

DOI:10.1139/v99-233

upstream raw materials:

2-<(cyclohexylmethyl)amino>-N-methyl-N-<2-(2-pyridinyl)ethyl>acetamide

4-bromo-pent-4-enoic acid

4-bromo-4-pentenoic acid tert-butyl ester

ethyl 2-<(cyclohexylmethyl)amino>acetate

Downstream raw materials:

2-(2-bromo-allyl)-N¹-[2-cyclohexyl-1-(5-isobutyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-N⁴-cyclohexylmethyl-N⁴-{[methyl-(2-pyridin-2-yl-ethyl)-carbamoyl]-methyl}-succinamide

N⁴-(cyclohexylmethyl)-N⁴-[2-[methyl[2-(2-pyridinyl)ethyl]amino]-2-oxoethyl]-N¹-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(S)-(2-bromo-2-propenyl)butanediamide

BILA 2157 BS

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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