4-[2-tert-butoxycarbonylamino-3-(4-methoxybenzylsulfanyl)-3-methoxycarbonylpropyl]benzoic acid tert-butyl ester

Base Information

• Chemical Name: 4-[2-tert-butoxycarbonylamino-3-(4-methoxybenzylsulfanyl)-3-methoxycarbonylpropyl]benzoic acid tert-butyl ester
• CAS No.: 473259-73-3
• Molecular Formula: C₂₉H₃₉NO₇S
• Molecular Weight: 545.697

Synonyms:4-[2-tert-butoxycarbonylamino-3-(4-methoxybenzylsulfanyl)-3-methoxycarbonylpropyl]benzoic acid tert-butyl ester

Chemical Property of 4-[2-tert-butoxycarbonylamino-3-(4-methoxybenzylsulfanyl)-3-methoxycarbonylpropyl]benzoic acid tert-butyl ester

Chemical Property:

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Technology Process of 4-[2-tert-butoxycarbonylamino-3-(4-methoxybenzylsulfanyl)-3-methoxycarbonylpropyl]benzoic acid tert-butyl ester

There total 6 articles about 4-[2-tert-butoxycarbonylamino-3-(4-methoxybenzylsulfanyl)-3-methoxycarbonylpropyl]benzoic acid tert-butyl 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: 54.0%

(p-methoxybenzyl-2,4-dinitrophenyl)disulfide (49621-83-2) + 4-(2-tert-butoxycarbonylamino-3-methoxycarbonylpropyl)benzoic acid tert-butyl ester (473259-72-2) → 4-[2-tert-butoxycarbonylamino-3-(4-methoxybenzylsulfanyl)-3-methoxycarbonylpropyl]benzoic acid tert-butyl ester (473259-73-3)

Guidance literature:

With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; at 0 ℃; for 0.25h;

4-(2-tert-butoxycarbonylamino-3-methoxycarbonylpropyl)benzoic acid tert-butyl ester; In tetrahydrofuran; hexane; at -70 ℃; for 2h;

(p-methoxybenzyl-2,4-dinitrophenyl)disulfide; With 1,6-Hexanediamine; In tetrahydrofuran; hexane; at -70 ℃; for 1.5h;

Reference yield: 47.0%

1-(4-methoxy-benzyldisulfanyl)-2,4-dinitrobenzene (191401-86-2) + 4-(2-tert-butoxycarbonylamino-3-methoxycarbonylpropyl)benzoic acid tert-butyl ester (473259-72-2) → 4-[2-tert-butoxycarbonylamino-3-(4-methoxybenzylsulfanyl)-3-methoxycarbonylpropyl]benzoic acid tert-butyl ester (473259-73-3)

Guidance literature:

4-(2-tert-butoxycarbonylamino-3-methoxycarbonylpropyl)benzoic acid tert-butyl ester; With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; at -70 ℃; for 2h;

1-(4-methoxy-benzyldisulfanyl)-2,4-dinitrobenzene; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; hexane; at -70 ℃; for 1.5h;

DOI:10.1021/jm0300680

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 4-[2-tert-butoxycarbonylamino-3-(4-methoxybenzylsulfanyl)-3-methoxycarbonylpropyl]benzoic acid tert-butyl ester (473259-73-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Et₃N / dimethylformamide / 48 h / 20 °C

2.1: 6.2 g / LiOH; LiBr; nBu₄NBr / acetonitrile / 20 °C

3.1: N-methylmorpholine / tetrahydrofuran / 0.25 h / -20 °C

4.1: tetrahydrofuran; diethyl ether / 2 h / 20 °C

4.2: 2.36 g / silver benzoate; Et₃N / 0.75 h / 0 - 20 °C

5.1: hexamethyldisilazane; nBuLi / tetrahydrofuran; hexane / 2 h / -70 °C

5.2: 47 percent / HMPA / tetrahydrofuran; hexane / 1.5 h / -70 °C

With 4-methyl-morpholine; lithium hydroxide; n-butyllithium; tetrabutylammomium bromide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; lithium bromide; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide; acetonitrile; 4.1: Arndt-Eistert homologation;

DOI:10.1021/jm0300680

upstream raw materials:

1-(4-methoxy-benzyldisulfanyl)-2,4-dinitrobenzene

4-(2-tert-butoxycarbonylamino-3-methoxycarbonylpropyl)benzoic acid tert-butyl ester

di-tert-butyl dicarbonate

4-(2-tert-butoxycarbonylamino-2-carboxyethyl)benzoic acid tert-butyl ester

Downstream raw materials:

4-{(2S)-2-amino-3-[1-(2S)-2-benzo[b]thiophen-3-yl-1-benzylcarbamoylethylcarbamoyl-(2S)-2-biphenyl-4-yl-ethylcarbamoyl]-3(S)-sulfanylpropyl}benzoic acid

4-[2-tert-butoxycarbonylamino-3-carboxy-3-(4-methoxybenzylsulfanyl)propyl]benzoic acid tert-butyl ester

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