ethyl 4-{3-[1-tert-butoxycarbonyl-3-(2-tert-butoxycarbonylaminoethyl)indol-4-yl]-2-methoxyphenyl}-3-oxobutanoate

Base Information

• Chemical Name: ethyl 4-{3-[1-tert-butoxycarbonyl-3-(2-tert-butoxycarbonylaminoethyl)indol-4-yl]-2-methoxyphenyl}-3-oxobutanoate
• CAS No.: 303068-09-9
• Molecular Formula: C₃₃H₄₂N₂O₈
• Molecular Weight: 594.705

Synonyms:ethyl 4-{3-[1-tert-butoxycarbonyl-3-(2-tert-butoxycarbonylaminoethyl)indol-4-yl]-2-methoxyphenyl}-3-oxobutanoate

Chemical Property of ethyl 4-{3-[1-tert-butoxycarbonyl-3-(2-tert-butoxycarbonylaminoethyl)indol-4-yl]-2-methoxyphenyl}-3-oxobutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of ethyl 4-{3-[1-tert-butoxycarbonyl-3-(2-tert-butoxycarbonylaminoethyl)indol-4-yl]-2-methoxyphenyl}-3-oxobutanoate

There total 15 articles about ethyl 4-{3-[1-tert-butoxycarbonyl-3-(2-tert-butoxycarbonylaminoethyl)indol-4-yl]-2-methoxyphenyl}-3-oxobutanoate 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: 99.0%

diazoacetic acid ethyl ester (623-73-4) + 3-[1-tert-butoxycarbonyl-3-(2-tert-butoxycarbonylaminoethyl)indol-4-yl]-2-methoxyphenylacetaldehyde (303068-08-8) → ethyl 4-{3-[1-tert-butoxycarbonyl-3-(2-tert-butoxycarbonylaminoethyl)indol-4-yl]-2-methoxyphenyl}-3-oxobutanoate (303068-09-9)

Guidance literature:

With tin(ll) chloride; In dichloromethane; at 20 ℃;

DOI:10.1039/b510653b

Reference yield:

2-bromo-6-(2-propenyl)phenol (17269-81-7) → ethyl 4-{3-[1-tert-butoxycarbonyl-3-(2-tert-butoxycarbonylaminoethyl)indol-4-yl]-2-methoxyphenyl}-3-oxobutanoate (303068-09-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 85 percent / K₂CO₃ / acetone / Heating

2.1: t-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

2.2: hexane; tetrahydrofuran / 1 h / 20 °C

3.1: 0.6 g / aq. HCl

4.1: 85 percent / aq. Na₂CO₃ / Pd(PPh₃)4 / 1,2-dimethoxy-ethane / Heating

5.1: 84 percent / OsCl₃; K₃Fe(CN)6; aq. K₂CO₃ / quinuclidine / 2-methyl-propan-2-ol / 48 h

6.1: 99 percent / aq. NaIO₄ / tetrahydrofuran / 2.5 h / 20 °C

7.1: 99 percent / SnCl₂ / CH₂Cl₂ / 20 °C

With hydrogenchloride; sodium periodate; osmium (III) chloride; tert.-butyl lithium; sodium carbonate; potassium carbonate; tin(ll) chloride; potassium hexacyanoferrate(III); Quinuclidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; acetone; tert-butyl alcohol; 4.1: Suzuki coupling;

DOI:10.1039/b510653b

Reference yield:

O-allyl-2-bromophenol (60333-75-7) → ethyl 4-{3-[1-tert-butoxycarbonyl-3-(2-tert-butoxycarbonylaminoethyl)indol-4-yl]-2-methoxyphenyl}-3-oxobutanoate (303068-09-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 100 percent / Et₂AlCl / hexane / 2.5 h / 20 °C

2.1: 85 percent / K₂CO₃ / acetone / Heating

3.1: t-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

3.2: hexane; tetrahydrofuran / 1 h / 20 °C

4.1: 0.6 g / aq. HCl

5.1: 85 percent / aq. Na₂CO₃ / Pd(PPh₃)4 / 1,2-dimethoxy-ethane / Heating

6.1: 84 percent / OsCl₃; K₃Fe(CN)6; aq. K₂CO₃ / quinuclidine / 2-methyl-propan-2-ol / 48 h

7.1: 99 percent / aq. NaIO₄ / tetrahydrofuran / 2.5 h / 20 °C

8.1: 99 percent / SnCl₂ / CH₂Cl₂ / 20 °C

With hydrogenchloride; sodium periodate; osmium (III) chloride; tert.-butyl lithium; diethylaluminium chloride; sodium carbonate; potassium carbonate; tin(ll) chloride; potassium hexacyanoferrate(III); Quinuclidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; acetone; tert-butyl alcohol; 1.1: Claisen rearrangement / 5.1: Suzuki coupling;

DOI:10.1039/b510653b

upstream raw materials:

diazoacetic acid ethyl ester

3-[1-tert-butoxycarbonyl-3-(2-tert-butoxycarbonylaminoethyl)indol-4-yl]-2-methoxyphenylacetaldehyde

4-bromo-3-(2-nitroethenyl)-indole

3-(2-tert-butoxycarbonylamino-ethyl)-4-[3-(2,3-dihydroxy-propyl)-2-methoxy-phenyl]-indole-1-carboxylic acid tert-butyl ester

Downstream raw materials:

(S)-ethyl 4-{3-[1-tert-butoxycarbonyl-3-(2-tert-butoxycarbonylaminoethyl)indol-4-yl]-2-methoxyphenyl}-2-(2-benzyloxycarbonylamino-3-methylbutanoylamino)-3-oxobutanoate

ethyl 4-{3-[1-tert-butoxycarbonyl-3-(2-tert-butoxycarbonylaminoethyl)indol-4-yl]-2-methoxyphenyl}-2-diazo-3-oxobutanoate

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