2-benzyloxycarbonylamino-3-(4-tert-butoxycarbonylamino-1H-indol-3-yl)-propionic acid

Base Information

• Chemical Name: 2-benzyloxycarbonylamino-3-(4-tert-butoxycarbonylamino-1H-indol-3-yl)-propionic acid
• CAS No.: 252288-59-8
• Molecular Formula: C₂₄H₂₇N₃O₆
• Molecular Weight: 453.495

Synonyms:2-benzyloxycarbonylamino-3-(4-tert-butoxycarbonylamino-1H-indol-3-yl)-propionic acid

Chemical Property of 2-benzyloxycarbonylamino-3-(4-tert-butoxycarbonylamino-1H-indol-3-yl)-propionic acid

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-benzyloxycarbonylamino-3-(4-tert-butoxycarbonylamino-1H-indol-3-yl)-propionic acid

There total 10 articles about 2-benzyloxycarbonylamino-3-(4-tert-butoxycarbonylamino-1H-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:

1-(N-triisopropylsilyl-1H-indol-3-yl)-N,N-dimethylmethanamine (146886-51-3) → 2-benzyloxycarbonylamino-3-(4-tert-butoxycarbonylamino-1H-indol-3-yl)-propionic acid (252288-59-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: tBuLi / diethyl ether / 1.75 h / -78 - 0 °C

1.2: 73 percent / diethyl ether / 1 h / -78 °C

2.1: 91.7 percent / tetrahydrofuran / 20 °C

3.1: MeI / dimethylformamide / 20 °C

4.1: 6.51 g / TBAF / tetrahydrofuran / 1 h / 20 °C

5.1: morpholine / Pd[PPh₃]4 / tetrahydrofuran / 0.5 h / 20 °C

6.1: 3.42 g / dioxane / 0.5 h / Heating

7.1: 39 percent / aq. NaOH; penicillin G acylase / aq. methanol / 37 °C / pH 7.6

8.1: dioxane; aq. NaOH / 1 h / 20 °C

With morpholine; sodium hydroxide; penicillin G acylase; tetrabutyl ammonium fluoride; tert.-butyl lithium; methyl iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; sodium hydroxide; diethyl ether; N,N-dimethyl-formamide; 4.1: Mannich-type reaction;

DOI:10.1002/1521-3765(20001103)6:21<3943::AID-CHEM3943<3.3.CO;2-K

Reference yield:

3-Dimethylaminomethyl-4-amino-1-triisopropylsilylindole (146886-61-5) → 2-benzyloxycarbonylamino-3-(4-tert-butoxycarbonylamino-1H-indol-3-yl)-propionic acid (252288-59-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 91.7 percent / tetrahydrofuran / 20 °C

2: MeI / dimethylformamide / 20 °C

3: 6.51 g / TBAF / tetrahydrofuran / 1 h / 20 °C

4: morpholine / Pd[PPh₃]4 / tetrahydrofuran / 0.5 h / 20 °C

5: 3.42 g / dioxane / 0.5 h / Heating

6: 39 percent / aq. NaOH; penicillin G acylase / aq. methanol / 37 °C / pH 7.6

7: dioxane; aq. NaOH / 1 h / 20 °C

With morpholine; sodium hydroxide; penicillin G acylase; tetrabutyl ammonium fluoride; methyl iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; sodium hydroxide; N,N-dimethyl-formamide; 3: Mannich-type reaction;

DOI:10.1002/1521-3765(20001103)6:21<3943::AID-CHEM3943<3.3.CO;2-K

Reference yield:

3-Dimethylaminomethyl-4-(N-tert-butyloxycarbonyl)amino-1-triisopropylsilylindole (252288-55-4) → 2-benzyloxycarbonylamino-3-(4-tert-butoxycarbonylamino-1H-indol-3-yl)-propionic acid (252288-59-8)

Guidance literature:

Multi-step reaction with 6 steps

1: MeI / dimethylformamide / 20 °C

2: 6.51 g / TBAF / tetrahydrofuran / 1 h / 20 °C

3: morpholine / Pd[PPh₃]4 / tetrahydrofuran / 0.5 h / 20 °C

4: 3.42 g / dioxane / 0.5 h / Heating

5: 39 percent / aq. NaOH; penicillin G acylase / aq. methanol / 37 °C / pH 7.6

6: dioxane; aq. NaOH / 1 h / 20 °C

With morpholine; sodium hydroxide; penicillin G acylase; tetrabutyl ammonium fluoride; methyl iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; sodium hydroxide; N,N-dimethyl-formamide; 2: Mannich-type reaction;

DOI:10.1002/1521-3765(20001103)6:21<3943::AID-CHEM3943<3.3.CO;2-K

upstream raw materials:

dibenzyl dicarbonate

(S)-4-(N-tert-Butyloxycarbonyl)aminotryptophan

3-(Dimethylaminomethyl)indole

1-(N-triisopropylsilyl-1H-indol-3-yl)-N,N-dimethylmethanamine

Downstream raw materials:

(S)-(2-(4-amino-1H-indol-3-yl)-1-(hydroxymethyl)ethyl)carbamic acid, phenylmethyl ester

(S,S)-(2-(4-((1-(((phenylmethyl)oxy)carbonyl)-2-methylpropyl)amino)-1H-indol-3-yl)-1-(hydroxymethyl)ethyl)carbamic acid, phenylmethyl ester

(-)-N¹³-Desmethyl-C¹²-desisopropyl-C¹²-phenylmethylindolactam V

(S)-N-Benzyloxycarbonyl-4-aminotryptophan methyl ester

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