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

Base Information

• Chemical Name: 3-(6-<5-<(2-tert-butoxycarbonylamino-acetylamino)methyl>-2,3-dimethoxyphenyl>-3H-indol-3-yl)-propionic acid
• CAS No.: 226888-42-2
• Molecular Formula: C₂₇H₃₃N₃O₇
• Molecular Weight: 511.575

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

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

Chemical Property:

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

There total 9 articles about 3-(6-<5-<(2-tert-butoxycarbonylamino-acetylamino)methyl>-2,3-dimethoxyphenyl>-3H-indol-3-yl)-propionic acid 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: 97.0%

3-(6-<5-<(2-tert-butoxycarbonylamino-acetylamino)methyl>-2,3-dimethoxyphenyl>-3H-indol-3-yl)-propionic acid ethyl ester (226888-31-9) → 3-(6-<5-<(2-tert-butoxycarbonylamino-acetylamino)methyl>-2,3-dimethoxyphenyl>-3H-indol-3-yl)-propionic acid (226888-42-2)

Guidance literature:

With potassium hydroxide; In ethanol; for 22h; Ambient temperature;

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

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 (226888-42-2)

Guidance literature:

Multi-step reaction with 8 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

8: 97 percent / aq. KOH / ethanol / 22 h / Ambient temperature

With piperidine; bismuth(III) chloride; potassium hydroxide; 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)-acrylic acid methyl ester (226888-27-3) → 3-(6-<5-<(2-tert-butoxycarbonylamino-acetylamino)methyl>-2,3-dimethoxyphenyl>-3H-indol-3-yl)-propionic acid (226888-42-2)

Guidance literature:

Multi-step reaction with 7 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

7: 97 percent / aq. KOH / ethanol / 22 h / Ambient temperature

With bismuth(III) chloride; potassium hydroxide; 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:

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

BOC-glycine

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

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

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