(R)-N-acetyl-4-bromotryptophan methyl ester

Base Information

• Chemical Name: (R)-N-acetyl-4-bromotryptophan methyl ester
• CAS No.: 343846-36-6
• Molecular Formula: C₁₄H₁₅BrN₂O₃
• Molecular Weight: 339.189
• Mol file: 343846-36-6.mol

Synonyms:(R)-N-acetyl-4-bromotryptophan methyl ester

Chemical Property of (R)-N-acetyl-4-bromotryptophan methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (R)-N-acetyl-4-bromotryptophan methyl ester

There total 1 articles about (R)-N-acetyl-4-bromotryptophan methyl ester 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: 47.0%

N-acetyl-4-bromo-DL-tryptophan (252026-08-7) + diazomethyl-trimethyl-silane (18107-18-1) → (S)-2-amino-3-(4-bromo-1H-indol-3-yl)propanoic acid (52448-16-5) + (R)-N-acetyl-4-bromotryptophan methyl ester (343846-36-6)

Guidance literature:

N-acetyl-4-bromo-DL-tryptophan; With acylase from Aspergillus genus; cobalt(II) chloride; In phosphate buffer; at 37 ℃; for 48h; pH=7.51;

diazomethyl-trimethyl-silane; In methanol; hexane; ethyl acetate; at 20 ℃; for 0.5h;

DOI:10.3987/COM-00-9137

Reference yield: 93.0%

p-toluenesulfonyl chloride (98-59-9) + (R)-N-acetyl-4-bromotryptophan methyl ester (343846-36-6) → (R)-N-acetyl-4-bromo-1-tosyltryptophan methyl ester (343846-38-8)

Guidance literature:

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

DOI:10.3987/COM-00-9137

Reference yield:

(R)-N-acetyl-4-bromotryptophan methyl ester (343846-36-6) → N-(tert-butoxycarbonyl)-4-bromo-1-tosyl-D-tryptophan methyl ester (343846-40-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / cetyltrimethylammonium bromide; NaOH / 1,2-dichloro-ethane / 1 h / -20 °C

2: 95 percent / DMAP / tetrahydrofuran / 3 h / 20 °C

3: 98 percent / NH₂NH₂*H₂O / 1,2-dichloro-ethane; methanol / 48 h / 20 °C

With dmap; sodium hydroxide; cetyltrimethylammonim bromide; hydrazine hydrate; In tetrahydrofuran; methanol; 1,2-dichloro-ethane;

DOI:10.3987/COM-00-9137

upstream raw materials:

N-acetyl-4-bromo-DL-tryptophan

diazomethyl-trimethyl-silane

Downstream raw materials:

(R)-N-acetyl-4-bromo-1-tosyltryptophan methyl ester

N-(tert-butoxycarbonyl)-4-bromo-1-tosyl-D-tryptophan methyl ester

3-[4-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-2-tert-butoxycarbonylamino-propionic acid

N-(tert-butoxycarbonyl)-4-bromo-N-methyl-1-tosyl-D-tryptophan

Refernces