2-{2-[(2-tert-butoxycarbonylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-butyrylamino}-3-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid methyl ester

Base Information

Chemical Name:2-{2-[(2-tert-butoxycarbonylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-butyrylamino}-3-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid methyl ester
CAS No.:639457-71-9
Molecular Formula:C₄₀H₅₆N₄O₈S
Molecular Weight:752.973
Hs Code.:

2-{2-[(2-<i>tert</i>-butoxycarbonylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-butyrylamino}-3-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1<i>H</i>-indol-3-yl]-propionic acid methyl ester

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Chemical Property of 2-{2-[(2-tert-butoxycarbonylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-butyrylamino}-3-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid methyl ester

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Technology Process of 2-{2-[(2-tert-butoxycarbonylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-butyrylamino}-3-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid methyl ester

There total 5 articles about 2-{2-[(2-tert-butoxycarbonylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-butyrylamino}-3-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid 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:

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

: 639457-71-9
2-{2-[(2-tert-butoxycarbonylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-butyrylamino}-3-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid methyl 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: 96 percent / HOBt; EDC; DIEA / CH₂Cl₂ / 6 h / 0 - 20 °C

5: aq. HF / acetonitrile / 8 h / 20 °C

6: 763 mg / HATU; DIEA / CH₂Cl₂ / 24 h

With sodium hydroxide; hydrogen fluoride; tetra(n-butyl)ammonium hydrogensulfate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In 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

: 639457-71-9
2-{2-[(2-tert-butoxycarbonylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-butyrylamino}-3-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid methyl 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: 96 percent / HOBt; EDC; DIEA / CH₂Cl₂ / 6 h / 0 - 20 °C

6: aq. HF / acetonitrile / 8 h / 20 °C

7: 763 mg / HATU; DIEA / CH₂Cl₂ / 24 h

With sodium hydroxide; hydrogen fluoride; tetra(n-butyl)ammonium hydrogensulfate; benzotriazol-1-ol; hydrazine hydrate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.tet.2003.04.005

Reference yield:

: 738591-23-6
2-prenyl-Boc-L-Trp-OMe

: 639457-71-9
2-{2-[(2-tert-butoxycarbonylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-butyrylamino}-3-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

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

2: 88 percent / aq. HF / acetonitrile / 8 h / 20 °C

3: 96 percent / HOBt; EDC; DIEA / CH₂Cl₂ / 6 h / 0 - 20 °C

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

5: 763 mg / HATU; DIEA / CH₂Cl₂ / 24 h

With sodium hydroxide; hydrogen fluoride; tetra(n-butyl)ammonium hydrogensulfate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; acetonitrile;
DOI:10.1016/j.tet.2003.04.005