acetic acid 1-(2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-2-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-ethyl ester

Base Information

Chemical Name:acetic acid 1-(2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-2-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-ethyl ester
CAS No.:639457-65-1
Molecular Formula:C₃₄H₄₅N₃O₇S
Molecular Weight:639.813
Hs Code.:

acetic acid 1-(2-<i>tert</i>-butoxycarbonylamino-3-methyl-butyrylamino)-2-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1<i>H</i>-indol-3-yl]-ethyl ester

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Chemical Property of acetic acid 1-(2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-2-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-ethyl ester

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Technology Process of acetic acid 1-(2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-2-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-ethyl ester

There total 7 articles about acetic acid 1-(2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-2-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-ethyl 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:

: 546-67-8
lead(IV) tetraacetate

: 2-(2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid

: 639457-65-1
acetic acid 1-(2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-2-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-ethyl ester

Guidance literature:: With pyridine; copper diacetate; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1016/j.tet.2003.04.005

Reference yield:

: 184866-57-7
methyl 2-(3-methyl-2-butenyl)-L-tryprophan

: 639457-65-1
acetic acid 1-(2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-2-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: Et₃N / dimethylformamide / 45 °C

2: 63 percent / NaOH; NBu₄HSO₄ / CH₂Cl₂ / 1 h / Heating

3: 88 percent / aq. HF / acetonitrile / 8 h / 20 °C

4: 92 percent / 1-hydroxybenzotriazole (HOBt); EDC; N,N-diisopropylethylamine / dimethylformamide / 6 h / 0 - 20 °C

5: aq. LiOH / tetrahydrofuran / 1 h / 20 °C

6: Cu(OAc)2; pyridine / tetrahydrofuran / 2 h / 20 °C

With pyridine; lithium hydroxide; sodium hydroxide; copper diacetate; hydrogen fluoride; tetra(n-butyl)ammonium hydrogensulfate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.tet.2003.04.005

Reference yield:

: 184866-51-1
methyl N-phthaloyl-2-(3-methyl-2-butenyl)-L-tryptophan

: 639457-65-1
acetic acid 1-(2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-2-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: NH₂NH₂*H₂O / methanol; CH₂Cl₂

2: Et₃N / dimethylformamide / 45 °C

3: 63 percent / NaOH; NBu₄HSO₄ / CH₂Cl₂ / 1 h / Heating

4: 88 percent / aq. HF / acetonitrile / 8 h / 20 °C

5: 92 percent / 1-hydroxybenzotriazole (HOBt); EDC; N,N-diisopropylethylamine / dimethylformamide / 6 h / 0 - 20 °C

6: aq. LiOH / tetrahydrofuran / 1 h / 20 °C

7: Cu(OAc)2; pyridine / tetrahydrofuran / 2 h / 20 °C

With pyridine; lithium hydroxide; sodium hydroxide; copper diacetate; hydrogen fluoride; tetra(n-butyl)ammonium hydrogensulfate; benzotriazol-1-ol; hydrazine hydrate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.tet.2003.04.005