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

Base Information

• Chemical Name: ethyl 4-{3-[1-tert-butoxycarbonyl-3-(2-tert-butoxycarbonylaminoethyl)indol-4-yl]-2-methoxyphenyl}-2-diazo-3-oxobutanoate
• CAS No.: 303068-10-2
• Molecular Formula: C₃₃H₄₀N₄O₈
• Molecular Weight: 620.703

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

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

Chemical Property:

Purity/Quality:

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

There total 16 articles about ethyl 4-{3-[1-tert-butoxycarbonyl-3-(2-tert-butoxycarbonylaminoethyl)indol-4-yl]-2-methoxyphenyl}-2-diazo-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: 72.0%

ethyl 4-{3-[1-tert-butoxycarbonyl-3-(2-tert-butoxycarbonylaminoethyl)indol-4-yl]-2-methoxyphenyl}-3-oxobutanoate (303068-09-9) → ethyl 4-{3-[1-tert-butoxycarbonyl-3-(2-tert-butoxycarbonylaminoethyl)indol-4-yl]-2-methoxyphenyl}-2-diazo-3-oxobutanoate (303068-10-2)

Guidance literature:

With 4-acetamidobenzenesulfonyl azide; triethylamine; In acetonitrile;

DOI:10.1016/S0040-4039(00)01121-7

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}-2-diazo-3-oxobutanoate (303068-10-2)

Guidance literature:

Multi-step reaction with 8 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

8.1: 72 percent / 4-acetamidobenzenesulfonyl azide; Et₃N / acetonitrile / 20 °C

With hydrogenchloride; sodium periodate; osmium (III) chloride; 4-acetamidobenzenesulfonyl azide; tert.-butyl lithium; sodium carbonate; potassium carbonate; triethylamine; tin(ll) chloride; potassium hexacyanoferrate(III); Quinuclidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; acetone; acetonitrile; 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}-2-diazo-3-oxobutanoate (303068-10-2)

Guidance literature:

Multi-step reaction with 9 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

9.1: 72 percent / 4-acetamidobenzenesulfonyl azide; Et₃N / acetonitrile / 20 °C

With hydrogenchloride; sodium periodate; osmium (III) chloride; 4-acetamidobenzenesulfonyl azide; tert.-butyl lithium; diethylaluminium chloride; sodium carbonate; potassium carbonate; triethylamine; tin(ll) chloride; potassium hexacyanoferrate(III); Quinuclidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; acetone; acetonitrile; tert-butyl alcohol; 1.1: Claisen rearrangement / 5.1: Suzuki coupling;

DOI:10.1039/b510653b

upstream raw materials:

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

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

di-tert-butyl dicarbonate

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

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