(R)-2-(Acetylamino)-3-(4-bromo-1H-indol-3-yl)propionic acid

Base Information

• Chemical Name: (R)-2-(Acetylamino)-3-(4-bromo-1H-indol-3-yl)propionic acid
• CAS No.: 252026-09-8
• Molecular Formula: C13H13BrN2O3
• Molecular Weight: 325.162
• DSSTox Substance ID: DTXSID70451469
• Nikkaji Number: J1.189.356B
• Wikidata: Q82271514
• Mol file: 252026-09-8.mol

Synonyms:252026-09-8;N-Acetyl-4-bromo-D-tryptophan;CTK0I6926;DTXSID70451469;(R)-2-(Acetylamino)-3-(4-bromo-1H-indol-3-yl)propionic acid;(R)-2-Acetamido-3-(4-bromo-1H-indol-3-yl)propanoic acid

Chemical Property of (R)-2-(Acetylamino)-3-(4-bromo-1H-indol-3-yl)propionic acid

Chemical Property:

• XLogP3: 2.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 324.01095
• Heavy Atom Count: 19
• Complexity: 364

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CC1=CNC2=C1C(=CC=C2)Br)C(=O)O
• Isomeric SMILES: CC(=O)N[C@H](CC1=CNC2=C1C(=CC=C2)Br)C(=O)O

Technology Process of (R)-2-(Acetylamino)-3-(4-bromo-1H-indol-3-yl)propionic acid

There total 1 articles about (R)-2-(Acetylamino)-3-(4-bromo-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:

N-acetyl-4-bromo-DL-tryptophan (252026-08-7) → (S)-2-amino-3-(4-bromo-1H-indol-3-yl)propanoic acid (52448-16-5) + (R)-N-acetyl-4-bromotryptophan (252026-09-8)

Guidance literature:

With Aspergillus acylase; at 37 ℃; for 48h; pH=7.51;

DOI:10.1016/S0040-4039(99)01620-2

Reference yield: 88.0%

p-toluenesulfonyl chloride (98-59-9) + (R)-N-acetyl-4-bromotryptophan (252026-09-8) → 4-[4-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-ylmethyl]-2-methyl-2H-oxazol-5-one + 2-acetylamino-3-[4-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid

Guidance literature:

With sodium hydroxide; cetyltrimethylammonim bromide; In 1,2-dichloro-ethane; at -20 ℃; for 1h;

DOI:10.3987/COM-00-9137

upstream raw materials:

N-acetyl-4-bromo-DL-tryptophan