BOC-5-BROMO-L-TRYPTOPHAN

Base Information

• Chemical Name: BOC-5-BROMO-L-TRYPTOPHAN
• CAS No.: 75816-20-5
• Molecular Formula: C16H19BrN2O4
• Molecular Weight: 383.242
• Hs Code.: 2933990090
• Mol file: 75816-20-5.mol

Synonyms:BOC-5-BROMO-L-TRYPTOPHAN;L-Tryptophan, 5-bromo-N-[(1,1-dimethylethoxy)carbonyl]-

Chemical Property of BOC-5-BROMO-L-TRYPTOPHAN

Chemical Property:

• PSA: 91.42000
• LogP: 3.84170

Purity/Quality:

98%Min ^*data from raw suppliers

L-TRYPTOPHAN, 5-BROMO-N-[(1,1-DIMETHYLETHOXY)CARBONYL]- 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of BOC-5-BROMO-L-TRYPTOPHAN

There total 4 articles about BOC-5-BROMO-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: 81.0%

5-bromo-DL-tryptophan (6548-09-0,25197-99-3,93299-40-2) → N-t-butoxycarbonyl-5-bromotryptophan (75816-20-5,114873-17-5)

Guidance literature:

Reference yield: 71.0%

di-tert-butyl dicarbonate (24424-99-5) + 5-bromo-DL-tryptophan (6548-09-0,25197-99-3,93299-40-2) → N-t-butoxycarbonyl-5-bromotryptophan (75816-20-5,114873-17-5)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; for 20h; pH=9;

DOI:10.1021/acs.jmedchem.7b01245

Reference yield:

Nα-acetyl-5-bromo-D,L-tryptophan (75816-15-8) → N-t-butoxycarbonyl-5-bromotryptophan (75816-20-5,114873-17-5)

Guidance literature:

Multi-step reaction with 2 steps

1: cobalt(II) chloride hexahydrate; acylase I from porcine kidney / aq. phosphate buffer / 108 h / 37 °C / pH 7.4 / Enzymatic reaction

2: sodium hydroxide / 1,4-dioxane / 20 h / pH 9

With cobalt(II) chloride hexahydrate; acylase I from porcine kidney; sodium hydroxide; In 1,4-dioxane; aq. phosphate buffer;

DOI:10.1021/acs.jmedchem.7b01245

upstream raw materials:

5-bromo-DL-tryptophan

di-tert-butyl dicarbonate

(S)-7-bromo-tryptophan

N^α-acetyl-5-bromo-D,L-tryptophan

Refernces

• 1、 Marelli, Enrico,Renault, Yohann,Sharma, Sunil V.,Nolan, Steven P.,Goss, Rebecca J. M.. "Mild, Aqueous α-Arylation of Ketones: Towards New Diversification Tools for Halogenated Metabolites and Drug Molecules". . p. 3832 - 3836. Retrieved 2017/03/27.