N-trityl-6-chloro-L-tryptophan

Base Information

• Chemical Name: N-trityl-6-chloro-L-tryptophan
• CAS No.: 1028302-45-5
• Molecular Formula: C₃₀H₂₅ClN₂O₂
• Molecular Weight: 480.994
• Mol file: 1028302-45-5.mol

Synonyms:

Chemical Property of N-trityl-6-chloro-L-tryptophan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-trityl-6-chloro-L-tryptophan

There total 8 articles about N-trityl-6-chloro-L-tryptophan 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:

trityl chloride (76-83-5) + 6-chloro-DL-tryptophan (33468-35-8,17808-35-4) → N-trityl-6-chloro-L-tryptophan (1028302-45-5)

Guidance literature:

6-chloro-DL-tryptophan; With chloro-trimethyl-silane; In ethyl acetate; at 40 ℃; for 4h;

trityl chloride; With triethylamine; In ethyl acetate; at 40 ℃; for 12h;

DOI:10.1081/SCC-200026636

Reference yield:

6-chloro-3-methyl-1H-indole (158905-35-2) → N-trityl-6-chloro-L-tryptophan (1028302-45-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 96 percent / DMAP / acetonitrile / 0 - 20 °C

2.1: NBS; AIBN / CCl₄ / 2.5 h / Heating

3.1: 5.37 g / nBuLi / tetrahydrofuran; hexane / 5 h / -78 °C

4.1: HCl / tetrahydrofuran; H₂O / 2 h / 20 °C

4.2: 71 percent / HCl / ethyl acetate / 3 h / 0 °C

5.1: 96 percent / NaOH / ethanol; H₂O / 1 h / 40 °C

6.1: TMSCl / ethyl acetate / 4 h / 40 °C

6.2: NEt₃ / ethyl acetate / 12 h / 40 °C

With hydrogenchloride; dmap; sodium hydroxide; N-Bromosuccinimide; n-butyllithium; chloro-trimethyl-silane; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; tetrachloromethane; ethanol; hexane; water; ethyl acetate; acetonitrile;

DOI:10.1081/SCC-200026636

Reference yield:

6-chloro-3-methylindole-2-carboxylate (441801-03-2) → N-trityl-6-chloro-L-tryptophan (1028302-45-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 96 percent / copper powder / quinoline / 3 h / Heating

2.1: 96 percent / DMAP / acetonitrile / 0 - 20 °C

3.1: NBS; AIBN / CCl₄ / 2.5 h / Heating

4.1: 5.37 g / nBuLi / tetrahydrofuran; hexane / 5 h / -78 °C

5.1: HCl / tetrahydrofuran; H₂O / 2 h / 20 °C

5.2: 71 percent / HCl / ethyl acetate / 3 h / 0 °C

6.1: 96 percent / NaOH / ethanol; H₂O / 1 h / 40 °C

7.1: TMSCl / ethyl acetate / 4 h / 40 °C

7.2: NEt₃ / ethyl acetate / 12 h / 40 °C

With hydrogenchloride; dmap; sodium hydroxide; N-Bromosuccinimide; n-butyllithium; chloro-trimethyl-silane; 2,2'-azobis(isobutyronitrile); copper; In tetrahydrofuran; quinoline; tetrachloromethane; ethanol; hexane; water; ethyl acetate; acetonitrile;

DOI:10.1081/SCC-200026636

upstream raw materials:

trityl chloride

6-chloro-DL-tryptophan

6-chloro-3-methyl-1H-indole

6-chloro-3-methylindole-2-carboxylate

Downstream raw materials:

N-trityl-6-chloro-L-tryptophan tert-butyl ester

Refernces