6-Brom-N^α-(tert-butyloxycarbonyl)-N-<(3,4,5-triacetoxyphenyl)carbonylmethyl>tryptophanamid

Base Information

• Chemical Name: 6-Brom-N^α-(tert-butyloxycarbonyl)-N-<(3,4,5-triacetoxyphenyl)carbonylmethyl>tryptophanamid
• CAS No.: 85515-01-1
• Molecular Formula: C₃₀H₃₂BrN₃O₁₀
• Molecular Weight: 674.502

Synonyms:6-Brom-N^α-(tert-butyloxycarbonyl)-N-<(3,4,5-triacetoxyphenyl)carbonylmethyl>tryptophanamid

Chemical Property of 6-Brom-N^α-(tert-butyloxycarbonyl)-N-<(3,4,5-triacetoxyphenyl)carbonylmethyl>tryptophanamid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 6-Brom-N^α-(tert-butyloxycarbonyl)-N-<(3,4,5-triacetoxyphenyl)carbonylmethyl>tryptophanamid

There total 11 articles about 6-Brom-N^α-(tert-butyloxycarbonyl)-N-<(3,4,5-triacetoxyphenyl)carbonylmethyl>tryptophanamid 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: 86.0%

(S)-6-Brom-N-(tert-butyloxycarbonyl)tryptophan-pentafluorphenylester (85515-04-4) + 3,4,5-Triacetoxy-α-aminoacetophenon-hydrochlorid (97444-00-3) → 6-Brom-Nα-(tert-butyloxycarbonyl)-N-<(3,4,5-triacetoxyphenyl)carbonylmethyl>tryptophanamid (85515-01-1)

Guidance literature:

With triethylamine; at 0 ℃; for 0.5h;

DOI:10.1002/jlac.198519850414

Reference yield:

3,4,5-triacetoxybenzoyl chloride (70475-59-1) → 6-Brom-Nα-(tert-butyloxycarbonyl)-N-<(3,4,5-triacetoxyphenyl)carbonylmethyl>tryptophanamid (85515-01-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / NEt₃ / dioxane; diethyl ether / 12 h / 0 °C

2: 92 percent / 1N HCl / dioxane; diethyl ether / 0.25 h / 10 °C

3: 83 percent / KI, NaN₃ / acetone / 2 h / Ambient temperature

4: 0.5N HCl, H₂ / Pd/C (5percent) / ethanol; diethyl ether / 1 h / 2250.2 Torr

5: 86 percent / NEt₃ / 0.5 h / 0 °C

With hydrogenchloride; sodium azide; hydrogen; triethylamine; potassium iodide; palladium on activated charcoal; In 1,4-dioxane; diethyl ether; ethanol; acetone;

DOI:10.1002/jlac.198519850414

Reference yield:

2-Chlor-1-(3,4,5-triacetoxyphenyl)ethanon (97443-98-6) → 6-Brom-Nα-(tert-butyloxycarbonyl)-N-<(3,4,5-triacetoxyphenyl)carbonylmethyl>tryptophanamid (85515-01-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / KI, NaN₃ / acetone / 2 h / Ambient temperature

2: 0.5N HCl, H₂ / Pd/C (5percent) / ethanol; diethyl ether / 1 h / 2250.2 Torr

3: 86 percent / NEt₃ / 0.5 h / 0 °C

With hydrogenchloride; sodium azide; hydrogen; triethylamine; potassium iodide; palladium on activated charcoal; In diethyl ether; ethanol; acetone;

DOI:10.1002/jlac.198519850414

upstream raw materials:

(S)-6-Brom-N-(tert-butyloxycarbonyl)tryptophan-pentafluorphenylester

3,4,5-Triacetoxy-α-aminoacetophenon-hydrochlorid

6-bromo-1H-indole

3,4,5-triacetoxybenzoyl chloride

Downstream raw materials:

6-Brom-N-<2-hydroxy-2-(3,4,5-triacetoxyphenyl)ethyl>-N^α-(tert-butyloxycarbonyl)tryptophanamid

O,O',O''-Triacetyl-N-(tert-butyloxycarbonyl)clionamid

6-Brom-N^α-(tert-butyloxycarbonyl)-N-<2-(4-nitrophenylseleno)-2-(3,4,5-triacetoxyphenyl)ethyl>tryptophanamid

Tetraacetylclionamid

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