-6-(1H-indol-3-ylmethyl)-6-methyl-4,7,12-trioxo-10,14-diphenyl-13-oxa-3,5,8,11-tetraazatetradecanoic acid

Base Information

• Chemical Name: -6-(1H-indol-3-ylmethyl)-6-methyl-4,7,12-trioxo-10,14-diphenyl-13-oxa-3,5,8,11-tetraazatetradecanoic acid
• CAS No.: 144876-76-6
• Molecular Formula: C₃₁H₃₃N₅O₆
• Molecular Weight: 571.633

Synonyms:-6-(1H-indol-3-ylmethyl)-6-methyl-4,7,12-trioxo-10,14-diphenyl-13-oxa-3,5,8,11-tetraazatetradecanoic acid

Chemical Property of -6-(1H-indol-3-ylmethyl)-6-methyl-4,7,12-trioxo-10,14-diphenyl-13-oxa-3,5,8,11-tetraazatetradecanoic acid

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Technology Process of -6-(1H-indol-3-ylmethyl)-6-methyl-4,7,12-trioxo-10,14-diphenyl-13-oxa-3,5,8,11-tetraazatetradecanoic acid

There total 5 articles about -6-(1H-indol-3-ylmethyl)-6-methyl-4,7,12-trioxo-10,14-diphenyl-13-oxa-3,5,8,11-tetraazatetradecanoic acid 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: 92.0%

methyl -6-(1H-indol-3-ylmethyl)-6-methyl-4,7,12-trioxo-10,14-diphenyl-13-oxa-3,5,8,11-tetraazatetradecanoate (144876-70-0) → -6-(1H-indol-3-ylmethyl)-6-methyl-4,7,12-trioxo-10,14-diphenyl-13-oxa-3,5,8,11-tetraazatetradecanoic acid (144876-76-6)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 25 ℃;

DOI:10.1016/S0040-4020(01)86596-0

Reference yield:

((S)-2-Amino-1-phenyl-ethyl)-carbamic acid benzyl ester (130406-36-9,142854-51-1) → -6-(1H-indol-3-ylmethyl)-6-methyl-4,7,12-trioxo-10,14-diphenyl-13-oxa-3,5,8,11-tetraazatetradecanoic acid (144876-76-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide / 1) THF, EtOAc, 25 deg C, 2 h, 2) 25 deg C, 17 h

2: 80 percent / piperidine / dimethylformamide / 17 h / 0 °C

3: 79 percent / toluene; tetrahydrofuran / 16 h / 80 - 100 °C

4: 92 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 25 °C

With piperidine; lithium hydroxide; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)86596-0

Reference yield:

N-[(9H-fluoren-9-ylmethyloxy)-carbonyl]-α-methyl-DL-tryptophan (134558-28-4) → -6-(1H-indol-3-ylmethyl)-6-methyl-4,7,12-trioxo-10,14-diphenyl-13-oxa-3,5,8,11-tetraazatetradecanoic acid (144876-76-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide / 1) THF, EtOAc, 25 deg C, 2 h, 2) 25 deg C, 17 h

2: 80 percent / piperidine / dimethylformamide / 17 h / 0 °C

3: 79 percent / toluene; tetrahydrofuran / 16 h / 80 - 100 °C

4: 92 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 25 °C

With piperidine; lithium hydroxide; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)86596-0

upstream raw materials:

methyl -6-(1H-indol-3-ylmethyl)-6-methyl-4,7,12-trioxo-10,14-diphenyl-13-oxa-3,5,8,11-tetraazatetradecanoate

((S)-2-Amino-1-phenyl-ethyl)-carbamic acid benzyl ester

N-[(9H-fluoren-9-ylmethyloxy)-carbonyl]-α-methyl-DL-tryptophan

phenylmethyl -<2-<<2-amino-3-(1H-indol-3-yl)-2-methyl-1-oxopropyl>amino>-1-phenylethyl>carbamate

Downstream raw materials:

4-methyl-1-(phenylmethyl) -N-amino>ethyl>amino>ethyl>amino>carbonyl>glycyl>-L-aspartate

4-methyl -N--1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl>amino>carbonyl>glycyl>-L-aspartate

methyl <7S-(7α,10β,14α)>-14-(1H-indol-3-ylmethyl)-14-methyl-2,5,8,13-tetraoxo-10-phenyl-1,3,6,9,12-pentaazacyclotetradecane-7-acetate

<7S-(7α,10β,14α)>-14-(1H-indol-3-ylmethyl)-14-methyl-2,5,8,13-tetraoxo-10-phenyl-1,3,6,9,12-pentaazacyclotetradecane-7-acetic acid

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