(R)-N-Acetyl-6-Chloro-Trp-OMe

Base Information

• Chemical Name: (R)-N-Acetyl-6-Chloro-Trp-OMe
• CAS No.: 1235280-35-9
• Molecular Formula: C14H15ClN2O3
• Molecular Weight: 294.73
• Mol file: 1235280-35-9.mol

Synonyms:(R)-N-Acetyl-6-Chloro-Trp-OMe;(R)-methyl 2-acetamido-3-(6-chloro-1H-indol-3-yl)propanoate

Chemical Property of (R)-N-Acetyl-6-Chloro-Trp-OMe

Chemical Property:

• PSA: 74.68000
• LogP: 2.88180
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

(R)-N-Acetyl-6-chloro-trp-OMe ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (R)-N-Acetyl-6-Chloro-Trp-OMe

There total 4 articles about (R)-N-Acetyl-6-Chloro-Trp-OMe 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: 57.0%

6-chloroindole (17422-33-2) + Methyl 2-acetamidoacrylate (35356-70-8) → 6-chloro-Nα-acetyltryptophan methyl ester (1034402-47-5,1235280-35-9)

Guidance literature:

With ethylaluminum dichloride; In hexane; dichloromethane; at 0 ℃; for 2h;

DOI:10.1021/jo800881u

Reference yield:

Nα-acetyl-6-chloro-D,L-tryptophan (50517-10-7) + diazomethyl-trimethyl-silane (18107-18-1) → 6-chloro-Nα-acetyltryptophan methyl ester (1034402-47-5,1235280-35-9)

Guidance literature:

With acetic anhydride; acetic acid; In methanol; ethyl acetate; toluene; at 20 ℃; for 1h;

DOI:10.1016/j.bmc.2012.12.028

Reference yield:

6-chloroindole (17422-33-2) → 6-chloro-Nα-acetyltryptophan methyl ester (1034402-47-5,1235280-35-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetic acid / 3 h / 45 °C

1.2: Heating

2.1: acetic acid; acetic anhydride / methanol; ethyl acetate; toluene / 1 h / 20 °C

With acetic anhydride; acetic acid; In methanol; ethyl acetate; toluene; 1.2: |Michael Addition;

DOI:10.1016/j.bmc.2012.12.028

upstream raw materials:

6-chloroindole

Methyl 2-acetamidoacrylate

N^α-acetyl-6-chloro-D,L-tryptophan

diazomethyl-trimethyl-silane

Refernces

• 1、 Wang, Zhen,Wang, Dong-Chao,Xie, Ming-Sheng,Qu, Gui-Rong,Guo, Hai-Ming. "Enantioselective Synthesis of Fused Polycyclic Tropanes via Dearomative [3 + 2] Cycloaddition Reactions of 2-Nitrobenzofurans". supporting information. p. 164 - 167. Retrieved 2020/01/11.
• 2、 Angelini, Elena,Balsamini, Cesarino,Bartoccini, Francesca,Lucarini, Simone,Piersanti, Giovanni. "Switchable reactivity of acylated α,β-dehydroamino ester in the Friedel-Crafts alkylation of indoles by changing the lewis acid". . p. 5654 - 5657. Retrieved 2008/12/21.