2-[(2-acetylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-N-{2-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-vinyl}-butyramide

Base Information

Chemical Name:2-[(2-acetylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-N-{2-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-vinyl}-butyramide
CAS No.:639457-73-1
Molecular Formula:C₃₅H₄₆N₄O₅S
Molecular Weight:634.84
Hs Code.:

2-[(2-acetylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-<i>N</i>-{2-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1<i>H</i>-indol-3-yl]-vinyl}-butyramide

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Chemical Property of 2-[(2-acetylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-N-{2-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-vinyl}-butyramide

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Technology Process of 2-[(2-acetylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-N-{2-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-vinyl}-butyramide

There total 8 articles about 2-[(2-acetylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-N-{2-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-vinyl}-butyramide 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:

: Acetic acid 1-{(S)-2-[((S)-2-acetylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-butyrylamino}-2-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-ethyl ester

: 639457-73-1
2-[(2-acetylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-N-{2-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-vinyl}-butyramide

: 639457-81-1
2-[(2-acetylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-N-{2-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-vinyl}-butyramide

Guidance literature:: With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1016/j.tet.2003.04.005

Reference yield:

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

: 639457-73-1
2-[(2-acetylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-N-{2-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-vinyl}-butyramide

Guidance literature:: Multi-step reaction with 12 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

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

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

12.1: 83 mg / 1,5,7-triaza-bicyclo[4.4.0]dec-5-ene polystyrene / CH₂Cl₂ / 1 h / 0 °C

With pyridine; 2,6-dimethylpyridine; lithium hydroxide; sodium hydroxide; copper diacetate; trimethylsilyl trifluoromethanesulfonate; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; 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 tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.tet.2003.04.005

Reference yield:

: 639457-63-9
2-amino-3-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid methyl ester

: 639457-73-1
2-[(2-acetylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-N-{2-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-vinyl}-butyramide

Guidance literature:: Multi-step reaction with 8 steps

1.1: 96 percent / HOBt; EDC; DIEA / CH₂Cl₂ / 6 h / 0 - 20 °C

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

3.1: 763 mg / HATU; DIEA / CH₂Cl₂ / 24 h

4.1: 2,6-lutidine; TMSOTf / CH₂Cl₂ / 1 h / 20 °C

4.2: MeOH / 2 h

5.1: 570 mg / Et₃N / CH₂Cl₂ / 2 h

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

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

8.1: 83 mg / 1,5,7-triaza-bicyclo[4.4.0]dec-5-ene polystyrene / CH₂Cl₂ / 1 h / 0 °C

With pyridine; 2,6-dimethylpyridine; lithium hydroxide; copper diacetate; trimethylsilyl trifluoromethanesulfonate; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; hydrogen fluoride; 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 tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1016/j.tet.2003.04.005