(S)-methyl 2-(tert-butoxycarbonylamino)-3-(1-tosyl-1H-indol-3-yl)propanoate

Base Information

• Chemical Name: (S)-methyl 2-(tert-butoxycarbonylamino)-3-(1-tosyl-1H-indol-3-yl)propanoate
• CAS No.: 352352-02-4
• Molecular Formula: C₂₄H₂₈N₂O₆S
• Molecular Weight: 472.562

Synonyms:(S)-methyl 2-(tert-butoxycarbonylamino)-3-(1-tosyl-1H-indol-3-yl)propanoate

Chemical Property of (S)-methyl 2-(tert-butoxycarbonylamino)-3-(1-tosyl-1H-indol-3-yl)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (S)-methyl 2-(tert-butoxycarbonylamino)-3-(1-tosyl-1H-indol-3-yl)propanoate

There total 3 articles about (S)-methyl 2-(tert-butoxycarbonylamino)-3-(1-tosyl-1H-indol-3-yl)propanoate 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: 93.0%

methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate (141215-69-2,33900-28-6) + p-toluenesulfonyl chloride (98-59-9) → (S)-methyl 2-(tert-butoxycarbonylamino)-3-(1-tosyl-1H-indol-3-yl)propanoate (352352-02-4)

Guidance literature:

methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate; With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In dichloromethane; for 0.333333h; Reflux;

p-toluenesulfonyl chloride; In dichloromethane; for 2h; Reflux;

DOI:10.1002/anie.201813984

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (S)-methyl 2-(tert-butoxycarbonylamino)-3-(1-tosyl-1H-indol-3-yl)propanoate (352352-02-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

2: 87 percent / NaOH; NBu₄HSO₄ / CH₂Cl₂ / 1 h / Heating

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; triethylamine; In dichloromethane;

DOI:10.1016/j.tet.2003.04.005

Reference yield:

(S)-tryptophan methyl ester hydrochloride (7524-52-9,26988-71-6,5619-09-0,14907-27-8,41222-70-2,67557-19-1,109492-62-8) → (S)-methyl 2-(tert-butoxycarbonylamino)-3-(1-tosyl-1H-indol-3-yl)propanoate (352352-02-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

2: 87 percent / NaOH; NBu₄HSO₄ / CH₂Cl₂ / 1 h / Heating

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; triethylamine; In dichloromethane;

DOI:10.1016/j.tet.2003.04.005

upstream raw materials:

methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate

p-toluenesulfonyl chloride

di-tert-butyl dicarbonate

(S)-tryptophan methyl ester hydrochloride

Downstream raw materials:

2-{2-[(2-tert-butoxycarbonylamino-4-methyl-pentanoyl)-methyl-amino]-3-phenyl-propionylamino}-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid methyl ester

(S)-2-{(S)-2-[((S)-2-Acetylamino-4-methyl-pentanoyl)-methyl-amino]-3-phenyl-propionylamino}-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid methyl ester

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