methyl (2S,4RS)-2-benzyloxycarbonylamino-3-(2,3-dihydro-1H-indol-3-yl)propionate

Base Information

• Chemical Name: methyl (2S,4RS)-2-benzyloxycarbonylamino-3-(2,3-dihydro-1H-indol-3-yl)propionate
• CAS No.: 744203-12-1
• Molecular Formula: C₂₀H₂₂N₂O₄
• Molecular Weight: 354.406

Synonyms:methyl (2S,4RS)-2-benzyloxycarbonylamino-3-(2,3-dihydro-1H-indol-3-yl)propionate

Chemical Property of methyl (2S,4RS)-2-benzyloxycarbonylamino-3-(2,3-dihydro-1H-indol-3-yl)propionate

Chemical Property:

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Technology Process of methyl (2S,4RS)-2-benzyloxycarbonylamino-3-(2,3-dihydro-1H-indol-3-yl)propionate

There total 2 articles about methyl (2S,4RS)-2-benzyloxycarbonylamino-3-(2,3-dihydro-1H-indol-3-yl)propionate 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:

(S)-N-benzyloxycarbonyl-L-tryptophan methyl ester (2717-76-2,130812-44-1,130812-46-3) → methyl (2S,4RS)-2-benzyloxycarbonylamino-3-(2,3-dihydro-1H-indol-3-yl)propionate (744203-12-1)

Guidance literature:

With dimethylsulfide borane complex; trifluoroacetic acid; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/S0040-4039(01)01492-7

Reference yield:

N-carbobenzyloxy-L-tryptophane (7432-21-5) → methyl (2S,4RS)-2-benzyloxycarbonylamino-3-(2,3-dihydro-1H-indol-3-yl)propionate (744203-12-1)

Guidance literature:

Multi-step reaction with 2 steps

1: KHCO₃ / dimethylformamide / 6 h / 20 °C

2: 420 mg / BH₃*Me₂S; TFA / tetrahydrofuran / 0.17 h / 0 °C

With dimethylsulfide borane complex; potassium hydrogencarbonate; trifluoroacetic acid; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1055/s-2004-822390

Reference yield: 75.0%

1,1-dimethyl-2-propynyl acetate (1604-29-1) + methyl (2S,4RS)-2-benzyloxycarbonylamino-3-(2,3-dihydro-1H-indol-3-yl)propionate (744203-12-1) → 2-benzyloxycarbonylamino-3-[1-(1,1-dimethyl-prop-2-ynyl)-2,3-dihydro-1H-indol-3-yl]-propionic acid methyl ester (744203-13-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; copper(l) chloride; In tetrahydrofuran; at 50 ℃;

DOI:10.1016/S0040-4039(01)01492-7

upstream raw materials:

(S)-N-benzyloxycarbonyl-L-tryptophan methyl ester

N-carbobenzyloxy-L-tryptophane

Downstream raw materials:

2-benzyloxycarbonylamino-3-[1-(1,1-dimethyl-prop-2-ynyl)-2,3-dihydro-1H-indol-3-yl]-propionic acid methyl ester

methyl (2S)-2-benzyloxycarbonylamino-3-[1-(1,1-dimethylprop-2-ynyl)-1H-indol-3-yl]propionate

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