(S)-2-{(S)-2-[((S)-2-Acetylamino-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: (S)-2-{(S)-2-[((S)-2-Acetylamino-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.: 639457-72-0
• Molecular Formula: C₃₇H₅₀N₄O₇S
• Molecular Weight: 694.893

Synonyms:

Chemical Property of (S)-2-{(S)-2-[((S)-2-Acetylamino-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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-{(S)-2-[((S)-2-Acetylamino-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 8 articles about (S)-2-{(S)-2-[((S)-2-Acetylamino-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:

methyl 2-(3-methyl-2-butenyl)-L-tryprophan (184866-57-7) → (S)-2-{(S)-2-[((S)-2-Acetylamino-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 (639457-72-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: Et₃N / dimethylformamide / 45 °C

2.1: 63 percent / NaOH; NBu₄HSO₄ / CH₂Cl₂ / 1 h / Heating

3.1: 88 percent / aq. HF / acetonitrile / 8 h / 20 °C

4.1: 96 percent / HOBt; EDC; DIEA / CH₂Cl₂ / 6 h / 0 - 20 °C

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

6.1: 763 mg / HATU; DIEA / CH₂Cl₂ / 24 h

7.1: 2,6-lutidine; TMSOTf / CH₂Cl₂ / 1 h / 20 °C

7.2: MeOH / 2 h

8.1: 570 mg / Et₃N / CH₂Cl₂ / 2 h

With 2,6-dimethylpyridine; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; 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:

methyl N-phthaloyl-2-(3-methyl-2-butenyl)-L-tryptophan (184866-51-1) → (S)-2-{(S)-2-[((S)-2-Acetylamino-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 (639457-72-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NH₂NH₂*H₂O / methanol; CH₂Cl₂

2.1: Et₃N / dimethylformamide / 45 °C

3.1: 63 percent / NaOH; NBu₄HSO₄ / CH₂Cl₂ / 1 h / Heating

4.1: 88 percent / aq. HF / acetonitrile / 8 h / 20 °C

5.1: 96 percent / HOBt; EDC; DIEA / CH₂Cl₂ / 6 h / 0 - 20 °C

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

7.1: 763 mg / HATU; DIEA / CH₂Cl₂ / 24 h

8.1: 2,6-lutidine; TMSOTf / CH₂Cl₂ / 1 h / 20 °C

8.2: MeOH / 2 h

9.1: 570 mg / Et₃N / CH₂Cl₂ / 2 h

With 2,6-dimethylpyridine; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; 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:

2-prenyl-Boc-L-Trp-OMe (738591-23-6) → (S)-2-{(S)-2-[((S)-2-Acetylamino-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 (639457-72-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 63 percent / NaOH; NBu₄HSO₄ / CH₂Cl₂ / 1 h / Heating

2.1: 88 percent / aq. HF / acetonitrile / 8 h / 20 °C

3.1: 96 percent / HOBt; EDC; DIEA / CH₂Cl₂ / 6 h / 0 - 20 °C

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

5.1: 763 mg / HATU; DIEA / CH₂Cl₂ / 24 h

6.1: 2,6-lutidine; TMSOTf / CH₂Cl₂ / 1 h / 20 °C

6.2: MeOH / 2 h

7.1: 570 mg / Et₃N / CH₂Cl₂ / 2 h

With 2,6-dimethylpyridine; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; 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; acetonitrile;

DOI:10.1016/j.tet.2003.04.005

upstream raw materials:

acetic anhydride

methyl 2-(3-methyl-2-butenyl)-L-tryprophan

methyl N-phthaloyl-2-(3-methyl-2-butenyl)-L-tryptophan

2-prenyl-Boc-L-Trp-OMe

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