(1-{(R)-1-[(1R,3S,5S)-3-(2-Ethylcarbamoyl-phenyl)-8-aza-bicyclo[3.2.1]octane-8-carbonyl]-4-phenyl-butylcarbamoyl}-1-methyl-ethyl)-carbamic acid tert-butyl ester

Base Information

• Chemical Name: (1-{(R)-1-[(1R,3S,5S)-3-(2-Ethylcarbamoyl-phenyl)-8-aza-bicyclo[3.2.1]octane-8-carbonyl]-4-phenyl-butylcarbamoyl}-1-methyl-ethyl)-carbamic acid tert-butyl ester
• CAS No.: 185099-77-8
• Molecular Formula: C₃₆H₅₀N₄O₅
• Molecular Weight: 618.817

Synonyms:(1-{(R)-1-[(1R,3S,5S)-3-(2-Ethylcarbamoyl-phenyl)-8-aza-bicyclo[3.2.1]octane-8-carbonyl]-4-phenyl-butylcarbamoyl}-1-methyl-ethyl)-carbamic acid tert-butyl ester

Chemical Property of (1-{(R)-1-[(1R,3S,5S)-3-(2-Ethylcarbamoyl-phenyl)-8-aza-bicyclo[3.2.1]octane-8-carbonyl]-4-phenyl-butylcarbamoyl}-1-methyl-ethyl)-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (1-{(R)-1-[(1R,3S,5S)-3-(2-Ethylcarbamoyl-phenyl)-8-aza-bicyclo[3.2.1]octane-8-carbonyl]-4-phenyl-butylcarbamoyl}-1-methyl-ethyl)-carbamic acid tert-butyl ester

There total 11 articles about (1-{(R)-1-[(1R,3S,5S)-3-(2-Ethylcarbamoyl-phenyl)-8-aza-bicyclo[3.2.1]octane-8-carbonyl]-4-phenyl-butylcarbamoyl}-1-methyl-ethyl)-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: 71.0%

ethylamine (75-04-7,85404-22-4) + 2-{(1R,3R,5S)-8-[(R)-2-(2-tert-Butoxycarbonylamino-2-methyl-propionylamino)-5-phenyl-pentanoyl]-8-aza-bicyclo[3.2.1]oct-3-yl}-benzoic acid (185148-38-3) → (1-{(R)-1-[(1R,3S,5S)-3-(2-Ethylcarbamoyl-phenyl)-8-aza-bicyclo[3.2.1]octane-8-carbonyl]-4-phenyl-butylcarbamoyl}-1-methyl-ethyl)-carbamic acid tert-butyl ester (185099-77-8)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane;

DOI:10.1016/S0960-894X(03)00261-0

Reference yield:

2-bromobenzoic acid ethyl ester (6091-64-1) → (1-{(R)-1-[(1R,3S,5S)-3-(2-Ethylcarbamoyl-phenyl)-8-aza-bicyclo[3.2.1]octane-8-carbonyl]-4-phenyl-butylcarbamoyl}-1-methyl-ethyl)-carbamic acid tert-butyl ester (185099-77-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 42 percent / (Ph₃P)4Pd / toluene / Heating

2: 0.217 g / H₂ / 10 percent Pd/C / methanol / 20 h / 760 Torr

3: 100 percent / HCl / dioxane

4: EDC; HOBT; 4-methylmorpholine / 20 °C

5: 100 percent / HCl / ethyl acetate / 20 °C

6: EDC; HOBT; 4-methylmorpholine / CH₂Cl₂ / 20 °C

7: 96 percent / aq. NaOH / methanol

8: 71 percent / EDC; HOBT; N-methylmorpholine / CH₂Cl₂

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; ethyl acetate; toluene; 1: Stille coupling;

DOI:10.1016/S0960-894X(03)00261-0

Reference yield:

tert-butyl 3-(trimethylstannyl)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate → (1-{(R)-1-[(1R,3S,5S)-3-(2-Ethylcarbamoyl-phenyl)-8-aza-bicyclo[3.2.1]octane-8-carbonyl]-4-phenyl-butylcarbamoyl}-1-methyl-ethyl)-carbamic acid tert-butyl ester (185099-77-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 42 percent / (Ph₃P)4Pd / toluene / Heating

2: 0.217 g / H₂ / 10 percent Pd/C / methanol / 20 h / 760 Torr

3: 100 percent / HCl / dioxane

4: EDC; HOBT; 4-methylmorpholine / 20 °C

5: 100 percent / HCl / ethyl acetate / 20 °C

6: EDC; HOBT; 4-methylmorpholine / CH₂Cl₂ / 20 °C

7: 96 percent / aq. NaOH / methanol

8: 71 percent / EDC; HOBT; N-methylmorpholine / CH₂Cl₂

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; ethyl acetate; toluene; 1: Stille coupling;

DOI:10.1016/S0960-894X(03)00261-0

upstream raw materials:

ethylamine

2-{(1R,3R,5S)-8-[(R)-2-(2-tert-Butoxycarbonylamino-2-methyl-propionylamino)-5-phenyl-pentanoyl]-8-aza-bicyclo[3.2.1]oct-3-yl}-benzoic acid

Boc-Aib-OH

2-bromobenzoic acid ethyl ester

Downstream raw materials:

2-{(1R,3S,5S)-8-[(R)-2-(2-Amino-2-methyl-propionylamino)-5-phenyl-pentanoyl]-8-aza-bicyclo[3.2.1]oct-3-yl}-N-ethyl-benzamide

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