N^α-acetyl-5-bromo-D-tryptophan

Base Information

• Chemical Name: N^α-acetyl-5-bromo-D-tryptophan
• CAS No.: 75816-16-9
• Molecular Formula: C₁₃H₁₃BrN₂O₃
• Molecular Weight: 325.162
• Mol file: 75816-16-9.mol

Synonyms:N^α-acetyl-5-bromo-D-tryptophan

Chemical Property of N^α-acetyl-5-bromo-D-tryptophan

Chemical Property:

• Melting Point: 124-127 °C
• Boiling Point: 627.7±55.0 °C(Predicted)
• Density: 1.615±0.06 g/cm3(Predicted)

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N^α-acetyl-5-bromo-D-tryptophan

There total 1 articles about N^α-acetyl-5-bromo-D-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: 94.0%

Nα-acetyl-5-bromo-D,L-tryptophan (75816-15-8) → 5-bromo-DL-tryptophan (6548-09-0,25197-99-3,93299-40-2) + Nα-acetyl-5-bromo-D-tryptophan (75816-16-9)

Guidance literature:

With borate buffer; cobalt(II) chloride; at 37 ℃; for 48h; pH=8.0; Enzymatic reaction;

DOI:10.1016/j.tetlet.2008.02.120

Reference yield:

H-L-Phe-Gly-NH2 (38678-61-4) + Nα-acetyl-5-bromo-D-tryptophan (75816-16-9) → Ac-5-Br-D-Trp-Phe-Gly-NH2

Guidance literature:

N^α-acetyl-5-bromo-D-tryptophan; With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 0.166667h; Inert atmosphere; Schlenk technique;

H-L-Phe-Gly-NH₂; With N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; at 80 ℃; for 0.166667h; Inert atmosphere; Schlenk technique; Microwave irradiation;

DOI:10.1021/jm5002925

Reference yield:

Nα-acetyl-5-bromo-D-tryptophan (75816-16-9) → Bpoc-Asn-Phe-Phe-D-Thr(Br)-OH (108827-09-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 51 percent / 6M H₂SO₄ / 1 h / Heating

2: DIEA / dimethylformamide; ethyl acetate / 16 h / 8 °C

With sulfuric acid; N-ethyl-N,N-diisopropylamine; In ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

N^α-acetyl-5-bromo-D,L-tryptophan

Downstream raw materials:

Bpoc-Asn-Phe-Phe-D-Thr(Br)-OH

Refernces

• 1、 Blaser, Georg,Sanderson, John M.,Batsanov, Andrei S.,Howard, Judith A.K.. "The facile synthesis of a series of tryptophan derivatives". . p. 2795 - 2798. Retrieved 2008/09/19.