3-[3-(tert-Butoxycarbonylamino-methyl)-phenyl]-2-(2-{2-[(2R,5S)-5-(2-carboxy-ethyl)-3,6-dioxo-piperazin-2-yl]-acetylamino}-acetylamino)-propionic acid methyl ester

Base Information

• Chemical Name: 3-[3-(tert-Butoxycarbonylamino-methyl)-phenyl]-2-(2-{2-[(2R,5S)-5-(2-carboxy-ethyl)-3,6-dioxo-piperazin-2-yl]-acetylamino}-acetylamino)-propionic acid methyl ester
• CAS No.: 325774-13-8
• Molecular Formula: C₂₇H₃₇N₅O₁₀
• Molecular Weight: 591.618
• Mol file: 325774-13-8.mol

Synonyms:

Chemical Property of 3-[3-(tert-Butoxycarbonylamino-methyl)-phenyl]-2-(2-{2-[(2R,5S)-5-(2-carboxy-ethyl)-3,6-dioxo-piperazin-2-yl]-acetylamino}-acetylamino)-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[3-(tert-Butoxycarbonylamino-methyl)-phenyl]-2-(2-{2-[(2R,5S)-5-(2-carboxy-ethyl)-3,6-dioxo-piperazin-2-yl]-acetylamino}-acetylamino)-propionic acid methyl ester

There total 16 articles about 3-[3-(tert-Butoxycarbonylamino-methyl)-phenyl]-2-(2-{2-[(2R,5S)-5-(2-carboxy-ethyl)-3,6-dioxo-piperazin-2-yl]-acetylamino}-acetylamino)-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:

2-(2-{2-[(2R,5S)-5-(2-Benzyloxycarbonyl-ethyl)-3,6-dioxo-piperazin-2-yl]-acetylamino}-acetylamino)-3-[3-(tert-butoxycarbonylamino-methyl)-phenyl]-propionic acid methyl ester (325774-12-7) → 3-[3-(tert-Butoxycarbonylamino-methyl)-phenyl]-2-(2-{2-[(2R,5S)-5-(2-carboxy-ethyl)-3,6-dioxo-piperazin-2-yl]-acetylamino}-acetylamino)-propionic acid methyl ester (325774-13-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate;

DOI:10.1016/S0960-894X(02)00063-X

Reference yield:

L-glutamic acid dimethyl ester (6525-53-7,16422-27-8,40149-68-6) → 3-[3-(tert-Butoxycarbonylamino-methyl)-phenyl]-2-(2-{2-[(2R,5S)-5-(2-carboxy-ethyl)-3,6-dioxo-piperazin-2-yl]-acetylamino}-acetylamino)-propionic acid methyl ester (325774-13-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: DIEA; EDC; HOBt / CHCl₃

2.1: H₂ / 10 percent Pd/C / methanol

3.1: T / methanol

4.1: aq. NaOH / tetrahydrofuran

5.1: Cs₂CO₃ / methanol

5.2: dimethylformamide; methanol

6.1: 95 percent aq. TFA / 0 - 20 °C

7.1: DIEA; EDC; HOBt / dimethylformamide

8.1: H₂ / 10 percent Pd/C / ethyl acetate

With sodium hydroxide; hydrogen; benzotriazol-1-ol; caesium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; chloroform; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(02)00063-X

Reference yield:

(+/-)-3-cyanophenylalanine (63999-80-4) → 3-[3-(tert-Butoxycarbonylamino-methyl)-phenyl]-2-(2-{2-[(2R,5S)-5-(2-carboxy-ethyl)-3,6-dioxo-piperazin-2-yl]-acetylamino}-acetylamino)-propionic acid methyl ester (325774-13-8)

Guidance literature:

Multi-step reaction with 9 steps

1: SOCl₂ / -5 °C

2: aq. Na₂CO₃ / dioxane

3: H₂; AcOH / Pd/C

4: aq. NaHCO₃ / dioxane

5: H₂N-NH₂*AcOH / methanol / 50 °C

6: DIEA; EDC; HOBt / CHCl₃

7: H₂ / 10 percent Pd/C / methanol

8: DIEA; EDC; HOBt / dimethylformamide

9: H₂ / 10 percent Pd/C / ethyl acetate

With thionyl chloride; hydrogen; hydrazinium monoacetate; sodium hydrogencarbonate; sodium carbonate; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; chloroform; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(02)00063-X

upstream raw materials:

2-(2-{2-[(2R,5S)-5-(2-Benzyloxycarbonyl-ethyl)-3,6-dioxo-piperazin-2-yl]-acetylamino}-acetylamino)-3-[3-(tert-butoxycarbonylamino-methyl)-phenyl]-propionic acid methyl ester

L-glutamic acid dimethyl ester

(+/-)-3-cyanophenylalanine

2-Amino-3-(3-cyano-phenyl)-propionic acid methyl ester

Downstream raw materials:

3-[3-(tert-butoxycarbonylamino-methyl)-phenyl]-2-(2-{2-[5-(2-{2-[3-(tert-butoxycarbonylamino-methyl)-phenyl]-1-methoxycarbonyl-ethylcarbamoyl}-ethyl)-3,6-dioxo-piperazin-2-yl]-acetylamino}-acetylamino)-propionic acid methyl ester