[1R-(1α,2α,3β)]-3-benzoxycarbamoylmethyl-2-isopropylcyclopropane-1-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [1R-(1α,2α,3β)]-3-benzoxycarbamoylmethyl-2-isopropylcyclopropane-1-carbamic acid tert-butyl ester
• CAS No.: 443149-71-1
• Molecular Formula: C₂₀H₃₀N₂O₄
• Molecular Weight: 362.469

Synonyms:[1R-(1α,2α,3β)]-3-benzoxycarbamoylmethyl-2-isopropylcyclopropane-1-carbamic acid tert-butyl ester

Chemical Property of [1R-(1α,2α,3β)]-3-benzoxycarbamoylmethyl-2-isopropylcyclopropane-1-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of [1R-(1α,2α,3β)]-3-benzoxycarbamoylmethyl-2-isopropylcyclopropane-1-carbamic acid tert-butyl ester

There total 6 articles about [1R-(1α,2α,3β)]-3-benzoxycarbamoylmethyl-2-isopropylcyclopropane-1-carbamic 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:

[1S-(1α,2β,3α)]-2-formyl-3-isopropylcyclopropane-1-carboxylic acid N-methoxy-N-methyl amide (443149-67-5) → [1R-(1α,2α,3β)]-3-benzoxycarbamoylmethyl-2-isopropylcyclopropane-1-carbamic acid tert-butyl ester (443149-71-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.25 h / 0 °C

1.2: hexane; tetrahydrofuran / 0.5 h / -78 °C

2.1: KOH; water / ethanol / 26 h / Heating

3.1: mercury(II) chloride / H₂O / 2 h / 70 °C

4.1: triethylamine; isobutyl chloroformate / acetone; H₂O / 0.5 h / -10 °C

4.2: sodium azide / acetone; H₂O / 1 h / -10 °C

4.3: 16 h / Heating

5.1: NaOH; water / ethanol / 1 h / 75 °C

6.1: isobutyl chloroformate; triethylamine / tetrahydrofuran / 0.33 h / -10 °C

6.2: tetrahydrofuran / 12 h / 20 °C

With potassium hydroxide; sodium hydroxide; n-butyllithium; water; triethylamine; mercury dichloride; isobutyl chloroformate; In tetrahydrofuran; ethanol; hexane; water; acetone; 1.1: Peterson olefination / 4.3: Curtius reaction;

DOI:10.1021/jo0110698

Reference yield:

[1S-(1α,2α,3α)]-2-formyl-3-isopropylcyclopropane-1-carboxylic acid N-methoxy-N-methyl amide (443149-66-4) → [1R-(1α,2α,3β)]-3-benzoxycarbamoylmethyl-2-isopropylcyclopropane-1-carbamic acid tert-butyl ester (443149-71-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: triethylamine / methanol / 72 h / 70 °C

2.1: n-BuLi / hexane; tetrahydrofuran / 0.25 h / 0 °C

2.2: hexane; tetrahydrofuran / 0.5 h / -78 °C

3.1: KOH; water / ethanol / 26 h / Heating

4.1: mercury(II) chloride / H₂O / 2 h / 70 °C

5.1: triethylamine; isobutyl chloroformate / acetone; H₂O / 0.5 h / -10 °C

5.2: sodium azide / acetone; H₂O / 1 h / -10 °C

5.3: 16 h / Heating

6.1: NaOH; water / ethanol / 1 h / 75 °C

7.1: isobutyl chloroformate; triethylamine / tetrahydrofuran / 0.33 h / -10 °C

7.2: tetrahydrofuran / 12 h / 20 °C

With potassium hydroxide; sodium hydroxide; n-butyllithium; water; triethylamine; mercury dichloride; isobutyl chloroformate; In tetrahydrofuran; methanol; ethanol; hexane; water; acetone; 2.1: Peterson olefination / 5.3: Curtius reaction;

DOI:10.1021/jo0110698

Reference yield:

[1R-(1α,2α,3β)]-2-isopropyl-3-methoxycarbonylmethylcyclopropane-1-carboxylic acid (443149-69-7) → [1R-(1α,2α,3β)]-3-benzoxycarbamoylmethyl-2-isopropylcyclopropane-1-carbamic acid tert-butyl ester (443149-71-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine; isobutyl chloroformate / acetone; H₂O / 0.5 h / -10 °C

1.2: sodium azide / acetone; H₂O / 1 h / -10 °C

1.3: 16 h / Heating

2.1: NaOH; water / ethanol / 1 h / 75 °C

3.1: isobutyl chloroformate; triethylamine / tetrahydrofuran / 0.33 h / -10 °C

3.2: tetrahydrofuran / 12 h / 20 °C

With sodium hydroxide; water; triethylamine; isobutyl chloroformate; In tetrahydrofuran; ethanol; water; acetone; 1.3: Curtius reaction;

DOI:10.1021/jo0110698

upstream raw materials:

[1S-(1α,2α,3α)]-2-formyl-3-isopropylcyclopropane-1-carboxylic acid N-methoxy-N-methyl amide

[1S-(1α,2β,3α)]-2-formyl-3-isopropylcyclopropane-1-carboxylic acid N-methoxy-N-methyl amide

[1R-(1α,2α,3β)]-2-isopropyl-3-methoxycarbonylmethylcyclopropane-1-carboxylic acid

[1R-(1α,2α,3β)]-2-isopropyl-3-methoxycarbonylmethylcyclopropane-1-carbamic acid tert-butyl ester

Downstream raw materials:

N-{[1R-(1α,2α,3β)]-3-benzoxycarbamoylmethyl-2-isopropylcyclopropyl}-L-phenylalanine N'-methyl amide

N-{[1R-(1α,2α,3β)]-3-benzoxycarbamoylmethyl-2-isopropylcyclopropyl}-L-phenylalanine methyl ester

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