{6-[1-tert-butoxycarbonylamino-2-(1H-indol-3-yl)-ethyl]-3-oxo-piperazin-2-yl}-acetic acid methyl ester

Base Information

• Chemical Name: {6-[1-tert-butoxycarbonylamino-2-(1H-indol-3-yl)-ethyl]-3-oxo-piperazin-2-yl}-acetic acid methyl ester
• CAS No.: 477842-10-7
• Molecular Formula: C₂₂H₃₀N₄O₅
• Molecular Weight: 430.504

Synonyms:{6-[1-tert-butoxycarbonylamino-2-(1H-indol-3-yl)-ethyl]-3-oxo-piperazin-2-yl}-acetic acid methyl ester

Chemical Property of {6-[1-tert-butoxycarbonylamino-2-(1H-indol-3-yl)-ethyl]-3-oxo-piperazin-2-yl}-acetic acid methyl ester

Chemical Property:

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Technology Process of {6-[1-tert-butoxycarbonylamino-2-(1H-indol-3-yl)-ethyl]-3-oxo-piperazin-2-yl}-acetic acid methyl ester

There total 2 articles about {6-[1-tert-butoxycarbonylamino-2-(1H-indol-3-yl)-ethyl]-3-oxo-piperazin-2-yl}-acetic 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:

L-Phenylalanine amide (5241-58-7) + 2-[2-tert-butoxycarbonylamino-1-cyano-3-(1H-indol-3-yl)-propylamino]-succinic acid dimethyl ester → {6-[1-tert-butoxycarbonylamino-2-(1H-indol-3-yl)-ethyl]-3-oxo-piperazin-2-yl}-acetic acid methyl ester (477842-21-0) + {6-[1-tert-butoxycarbonylamino-2-(1H-indol-3-yl)-ethyl]-3-oxo-piperazin-2-yl}-acetic acid methyl ester (477842-10-7) + (S)-2-[(1S,2S)-2-tert-Butoxycarbonylamino-1-[((S)-1-carbamoyl-2-phenyl-ethylamino)-methyl]-3-(1H-indol-3-yl)-propylamino]-succinic acid dimethyl ester (438579-68-1) + (S)-2-[(1R,2S)-2-tert-Butoxycarbonylamino-1-[((S)-1-carbamoyl-2-phenyl-ethylamino)-methyl]-3-(1H-indol-3-yl)-propylamino]-succinic acid dimethyl ester (438579-67-0)

Guidance literature:

With hydrogen; triethylamine; palladium on activated charcoal; In methanol; at 20 ℃; for 8h; under 760 Torr;

DOI:10.1016/S0040-4039(02)00012-6

Reference yield:

methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) + 2-[2-tert-butoxycarbonylamino-1-cyano-3-(1H-indol-3-yl)-propylamino]-succinic acid dimethyl ester → {6-[1-tert-butoxycarbonylamino-2-(1H-indol-3-yl)-ethyl]-3-oxo-piperazin-2-yl}-acetic acid methyl ester (477842-21-0) + {6-[1-tert-butoxycarbonylamino-2-(1H-indol-3-yl)-ethyl]-3-oxo-piperazin-2-yl}-acetic acid methyl ester (477842-10-7) + (S)-2-{(1S,2S)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-1-[((S)-1-methoxycarbonyl-2-phenyl-ethylamino)-methyl]-propylamino}-succinic acid dimethyl ester + (S)-2-{(1R,2S)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-1-[((S)-1-methoxycarbonyl-2-phenyl-ethylamino)-methyl]-propylamino}-succinic acid dimethyl ester

Guidance literature:

With hydrogen; triethylamine; palladium on activated charcoal; In methanol; at 20 ℃; for 8h; under 760 Torr;

DOI:10.1016/S0040-4039(02)00012-6

Reference yield:

{6-[1-tert-butoxycarbonylamino-2-(1H-indol-3-yl)-ethyl]-3-oxo-piperazin-2-yl}-acetic acid methyl ester (477842-10-7) → [2-(1H-indol-3-yl)-1-(1,6,8-trioxo-7-phenyl-octahydro-pyrazino[1,2-c]pyrimidin-4-yl)-ethyl]-carbamic acid tert-butyl ester (477842-13-0)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 24 h

2: 90 percent / DBU / tetrahydrofuran / 20 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran;

DOI:10.1016/S0040-4039(02)00964-4

upstream raw materials:

L-Phenylalanine amide

methyl (2S)-2-amino-3-phenylpropanoate

Downstream raw materials:

{6-[1-tert-butoxycarbonylamino-2-(1H-indol-3-yl)-ethyl]-3-oxo-1-phenylcarbamoyl-piperazin-2-yl}-acetic acid methyl ester

[2-(1H-indol-3-yl)-1-(1,6,8-trioxo-7-phenyl-octahydro-pyrazino[1,2-c]pyrimidin-4-yl)-ethyl]-carbamic acid tert-butyl ester

[1-(7-benzyl-1,6,8-trioxo-octahydro-pyrazino[1,2-c]pyrimidin-4-yl)-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester

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