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

Base Information

• Chemical Name: 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
• CAS No.: 294856-63-6
• Molecular Formula: C₄₁H₆₅BrN₄O₅
• Molecular Weight: 773.895

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 17 articles about 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 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:

2-Methoxypropene (116-11-0) + 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 (294856-61-4) → 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 (294856-63-6)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 25 ℃; for 15h;

DOI:10.1139/v99-233

Reference yield:

4-bromo-pent-4-enoic acid (86953-48-2) → 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 (294856-63-6)

Guidance literature:

Multi-step reaction with 9 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

8.1: 59.9 percent / TBTU; i-Pr₂NEt / acetonitrile / 2 h / 15 - 25 °C

9.1: PPTS / CH₂Cl₂ / 15 h / 25 °C

With hydrogenchloride; n-butyllithium; oxalyl dichloride; lithium hydroperoxide; triphenylmethane; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; acetonitrile; 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 / 8.1: Condensation / 9.1: Condensation;

DOI:10.1139/v99-233

Reference yield:

4-bromo-4-pentenoic acid tert-butyl ester (92975-38-7) → 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 (294856-63-6)

Guidance literature:

Multi-step reaction with 10 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

9.1: 59.9 percent / TBTU; i-Pr₂NEt / acetonitrile / 2 h / 15 - 25 °C

10.1: PPTS / CH₂Cl₂ / 15 h / 25 °C

With hydrogenchloride; n-butyllithium; oxalyl dichloride; lithium hydroperoxide; triphenylmethane; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; acetonitrile; 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 / 9.1: Condensation / 10.1: Condensation;

DOI:10.1139/v99-233

upstream raw materials:

2-Methoxypropene

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

4-bromo-pent-4-enoic acid

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

Downstream raw materials:

BILA 2157 BS

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