3-(6-<5-<(2-tert-butoxycarbonylamino-acetylamino)methyl>-2,3-dimethoxyphenyl>-3H-indol-3-yl)-propionic acid ethyl ester

Base Information

• Chemical Name: 3-(6-<5-<(2-tert-butoxycarbonylamino-acetylamino)methyl>-2,3-dimethoxyphenyl>-3H-indol-3-yl)-propionic acid ethyl ester
• CAS No.: 226888-31-9
• Molecular Formula: C₂₉H₃₇N₃O₇
• Molecular Weight: 539.629

Synonyms:3-(6-<5-<(2-tert-butoxycarbonylamino-acetylamino)methyl>-2,3-dimethoxyphenyl>-3H-indol-3-yl)-propionic acid ethyl ester

Chemical Property of 3-(6-<5-<(2-tert-butoxycarbonylamino-acetylamino)methyl>-2,3-dimethoxyphenyl>-3H-indol-3-yl)-propionic acid ethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of 3-(6-<5-<(2-tert-butoxycarbonylamino-acetylamino)methyl>-2,3-dimethoxyphenyl>-3H-indol-3-yl)-propionic acid ethyl ester

There total 7 articles about 3-(6-<5-<(2-tert-butoxycarbonylamino-acetylamino)methyl>-2,3-dimethoxyphenyl>-3H-indol-3-yl)-propionic acid ethyl 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:

6-bromo-1H-indole-3-carbaldehyde (17826-04-9) → 3-(6-<5-<(2-tert-butoxycarbonylamino-acetylamino)methyl>-2,3-dimethoxyphenyl>-3H-indol-3-yl)-propionic acid ethyl ester (226888-31-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 97 percent / piperidine / pyridine / 24 h / 50 °C

2: 75 percent / BiCl₃, NaBH₄ / aq. ethanol / 24 h / 0 °C

3: 71 percent / Na₂CO₃, Pd(PPh₃)4 / ethanol; 1,2-dimethoxy-ethane / 24 h / Heating

4: 94 percent / NaBH₄ / methanol / 0.25 h

5: 85 percent / DPPA, DBU / toluene / 2 h / 0 °C

6: H₂ / Pd/CaCO₃ / ethanol

7: HOBT, EDC / dimethylformamide

With piperidine; bismuth(III) chloride; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diphenyl-phosphinic acid; hydrogen; sodium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1,8-diazabicyclo[5.4.0]undec-7-ene; Lindlar's catalyst; In pyridine; methanol; 1,2-dimethoxyethane; ethanol; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(99)00171-4

Reference yield:

3-(6-bromo-3H-indol-3-yl)-propionic acid methyl ester (210889-33-1) → 3-(6-<5-<(2-tert-butoxycarbonylamino-acetylamino)methyl>-2,3-dimethoxyphenyl>-3H-indol-3-yl)-propionic acid ethyl ester (226888-31-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 71 percent / Na₂CO₃, Pd(PPh₃)4 / ethanol; 1,2-dimethoxy-ethane / 24 h / Heating

2: 94 percent / NaBH₄ / methanol / 0.25 h

3: 85 percent / DPPA, DBU / toluene / 2 h / 0 °C

4: H₂ / Pd/CaCO₃ / ethanol

5: HOBT, EDC / dimethylformamide

With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diphenyl-phosphinic acid; hydrogen; sodium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1,8-diazabicyclo[5.4.0]undec-7-ene; Lindlar's catalyst; In methanol; 1,2-dimethoxyethane; ethanol; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(99)00171-4

Reference yield:

3-(6-bromo-3H-indol-3-yl)-acrylic acid methyl ester (226888-27-3) → 3-(6-<5-<(2-tert-butoxycarbonylamino-acetylamino)methyl>-2,3-dimethoxyphenyl>-3H-indol-3-yl)-propionic acid ethyl ester (226888-31-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 75 percent / BiCl₃, NaBH₄ / aq. ethanol / 24 h / 0 °C

2: 71 percent / Na₂CO₃, Pd(PPh₃)4 / ethanol; 1,2-dimethoxy-ethane / 24 h / Heating

3: 94 percent / NaBH₄ / methanol / 0.25 h

4: 85 percent / DPPA, DBU / toluene / 2 h / 0 °C

5: H₂ / Pd/CaCO₃ / ethanol

6: HOBT, EDC / dimethylformamide

With bismuth(III) chloride; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diphenyl-phosphinic acid; hydrogen; sodium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1,8-diazabicyclo[5.4.0]undec-7-ene; Lindlar's catalyst; In methanol; 1,2-dimethoxyethane; ethanol; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(99)00171-4

upstream raw materials:

BOC-glycine

6-bromo-1H-indole-3-carbaldehyde

3-(6-bromo-3H-indol-3-yl)-propionic acid methyl ester

3-(6-bromo-3H-indol-3-yl)-acrylic acid methyl ester

Downstream raw materials:

3-(6-<5-<(2-tert-butoxycarbonylamino-acetylamino)methyl>-2,3-dimethoxyphenyl>-3H-indol-3-yl)-propionic acid

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