(R)-3-[(R)-2-[((S)-2-Amino-propionyl)-methyl-amino]-3-(2-bromo-1H-indol-3-yl)-propionylamino]-3-(4-methoxy-phenyl)-propionic acid methyl ester

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Chemical Name:(R)-3-[(R)-2-[((S)-2-Amino-propionyl)-methyl-amino]-3-(2-bromo-1H-indol-3-yl)-propionylamino]-3-(4-methoxy-phenyl)-propionic acid methyl ester
CAS No.:134781-91-2
Molecular Formula:C₂₆H₃₁BrN₄O₅
Molecular Weight:559.46
Hs Code.:

Synonyms:(R)-3-[(R)-2-[((S)-2-Amino-propionyl)-methyl-amino]-3-(2-bromo-1H-indol-3-yl)-propionylamino]-3-(4-methoxy-phenyl)-propionic acid methyl ester

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Chemical Property of (R)-3-[(R)-2-[((S)-2-Amino-propionyl)-methyl-amino]-3-(2-bromo-1H-indol-3-yl)-propionylamino]-3-(4-methoxy-phenyl)-propionic acid methyl ester

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Technology Process of (R)-3-[(R)-2-[((S)-2-Amino-propionyl)-methyl-amino]-3-(2-bromo-1H-indol-3-yl)-propionylamino]-3-(4-methoxy-phenyl)-propionic acid methyl ester

There total 12 articles about (R)-3-[(R)-2-[((S)-2-Amino-propionyl)-methyl-amino]-3-(2-bromo-1H-indol-3-yl)-propionylamino]-3-(4-methoxy-phenyl)-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: 67.0%

: 131791-80-5
N-Boc-(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-methyl-(R)-β-tyrosine Methyl Ester

: 134781-91-2
(R)-3-[(R)-2-[((S)-2-Amino-propionyl)-methyl-amino]-3-(2-bromo-1H-indol-3-yl)-propionylamino]-3-(4-methoxy-phenyl)-propionic acid methyl ester

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 0.666667h;
DOI:10.1021/jo00017a037

Reference yield:

: 696-62-8
para-iodoanisole

: 134781-91-2
(R)-3-[(R)-2-[((S)-2-Amino-propionyl)-methyl-amino]-3-(2-bromo-1H-indol-3-yl)-propionylamino]-3-(4-methoxy-phenyl)-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 78 percent / NEt₃, Pd(OAc)2, tri-o-tolylphosphine / dimethylformamide / 24 h / Heating

2: 65 percent / NaBH₄, 9 N HCl / tetrahydrofuran; aq. ethanol / 1.) pH 7, -35 deg C, 1 h, 2.) -20 deg C, overnight

3: 81 percent / 4.5 N HCl / 2.5 h / 100 °C

4: 100 percent / HCl gas / 0 - 5 °C

5: 84 percent / triethylamine, DCC / tetrahydrofuran / Ambient temperature

6: 67 percent / trifluoroacetic acid / CH₂Cl₂ / 0.67 h / 0 °C

With hydrogenchloride; palladium diacetate; sodium tetrahydroborate; triethylamine; dicyclohexyl-carbodiimide; tris-(o-tolyl)phosphine; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00017a037

Reference yield:

: 131831-87-3
N-methyl-(R)-tryptophan methyl ester

: 134781-91-2
(R)-3-[(R)-2-[((S)-2-Amino-propionyl)-methyl-amino]-3-(2-bromo-1H-indol-3-yl)-propionylamino]-3-(4-methoxy-phenyl)-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / DCC/HOBt / tetrahydrofuran / 24 h / 4 °C

2: 78 percent / benzoyl peroxide, N-bromosuccinimide / CH₂Cl₂ / 0.5 h / 0 °C

3: 99 percent / Na₂CO₃ / methanol; H₂O / 1 h / 70 °C

4: 84 percent / triethylamine, DCC / tetrahydrofuran / Ambient temperature

5: 67 percent / trifluoroacetic acid / CH₂Cl₂ / 0.67 h / 0 °C

With N-Bromosuccinimide; sodium carbonate; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; dibenzoyl peroxide; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/jo00017a037