N-Chloroacetyl-L-tryptophan

Base Information

• Chemical Name: N-Chloroacetyl-L-tryptophan
• CAS No.: 64709-57-5
• Molecular Formula: C13H13ClN2O3
• Molecular Weight: 280.711
• Hs Code.: 2933990090
• European Community (EC) Number: 265-029-5
• DSSTox Substance ID: DTXSID401304334
• Nikkaji Number: J208.173C
• Wikidata: Q76009771
• Mol file: 64709-57-5.mol

Synonyms:CA-Trp;chloroacetyl-L-tryptophan;chloroacetyltryptophan;chloroacetyltryptophan, (DL)-isomer

Chemical Property of N-Chloroacetyl-L-tryptophan

Chemical Property:

• Vapor Pressure: 9.66E-16mmHg at 25°C
• Melting Point: 163 °C
• Refractive Index: 24 ° (C=2, MeOH)
• Boiling Point: 610.2 °C at 760 mmHg
• PKA: 3.22±0.10(Predicted)
• Flash Point: 322.8 °C
• PSA: 82.19000
• Density: 1.428 g/cm³
• LogP: 1.90950
• Storage Temp.: −20°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 280.0614700
• Heavy Atom Count: 19
• Complexity: 351

Purity/Quality:

98.5% ^*data from raw suppliers

(S)-2-(2-Chloroacetamido)-3-(1H-indol-3-yl)propanoicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CC(C(=O)O)NC(=O)CCl
• Isomeric SMILES: C1=CC=C2C(=C1)C(=CN2)C[C@@H](C(=O)O)NC(=O)CCl

Technology Process of N-Chloroacetyl-L-tryptophan

There total 1 articles about N-Chloroacetyl-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%

chloroacetyl chloride (79-04-9) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → 2-(2-chloroacetamido)-3-(1H-indol-3-yl)propanoic acid (64709-57-5)

Guidance literature:

With sodium hydroxide; for 0.166667h;

DOI:10.1039/P19920000797

Reference yield: 89.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 2-(2-chloroacetamido)-3-(1H-indol-3-yl)propanoic acid (64709-57-5) → (S)-methyl-2-(2-chloro-acetylamino)-3-(1H-indol-3-yl)propanoate (108273-71-8)

Guidance literature:

In methanol; diethyl ether;

DOI:10.1039/P19920000797

Reference yield:

2-(2-chloroacetamido)-3-(1H-indol-3-yl)propanoic acid (64709-57-5) → 4-(tert-butyldiphenylsiloxymethyl)-1,3,4,5,6,7-hexahydro-6-oxopyrrolo<4,3,2-fg><3>benzazocine (141734-67-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) irradiation, H₂O, 45 min, 2) MeOH, Et₂O

2: 61 percent / NaBH₄ / ethanol; H₂O / 0.5 h

3: 76 percent / imidazole / dimethylformamide / 15 h

With 1H-imidazole; sodium tetrahydroborate; In ethanol; water; N,N-dimethyl-formamide;

DOI:10.1039/P19920000797

upstream raw materials:

chloroacetyl chloride

L-Tryptophan

Downstream raw materials:

N^α-iodoacetyl-L-tryptophan

(S)-methyl-2-(2-chloro-acetylamino)-3-(1H-indol-3-yl)propanoate

(S)-2-(2-Benzoylsulfanyl-acetylamino)-3-(1H-indol-3-yl)-propionic acid

4-(tert-butyldiphenylsiloxymethyl)-1,3,4,5,6,7-hexahydro-6-oxopyrrolo<4,3,2-fg><3>benzazocine

Refernces

• 1、 Singh, Thokchom Prasanta,Shunmugam, Raja. "PCl3-mediated synthesis of green/cyan fluorescent protein chromophores using amino acids". supporting information. p. 3024 - 3027. Retrieved 2016/05/09.
• 2、 Oya,Matsumoto,Takashina,Watanabe,Iwao. "Thiol compounds. II. Synthesis and antihypertensive activity of mercaptoacylamino acids". . p. 940 - 947. Retrieved 2007/10/02.