DL-Phenylalanine, 3-cyano-, methyl ester

Base Information

• Chemical Name: DL-Phenylalanine, 3-cyano-, methyl ester
• CAS No.: 164648-62-8
• Molecular Formula: C₁₁H₁₂N₂O₂
• Molecular Weight: 204.228
• Mol file: 164648-62-8.mol

Synonyms:

Chemical Property of DL-Phenylalanine, 3-cyano-, methyl ester

Chemical Property:

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of DL-Phenylalanine, 3-cyano-, methyl ester

There total 1 articles about DL-Phenylalanine, 3-cyano-, 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:

methanol (67-56-1) + (+/-)-3-cyanophenylalanine (63999-80-4) → 2-Amino-3-(3-cyano-phenyl)-propionic acid methyl ester (164648-62-8)

Guidance literature:

With thionyl chloride; at -5 ℃;

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

Reference yield:

2-Amino-3-(3-cyano-phenyl)-propionic acid methyl ester (164648-62-8) → 3-(3-Aminomethyl-phenyl)-2-{2-[2-((2R,5S)-5-{2-[2-(3-aminomethyl-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-ethyl}-3,6-dioxo-piperazin-2-yl)-acetylamino]-acetylamino}-propionic acid methyl ester

Guidance literature:

Multi-step reaction with 10 steps

1: aq. Na₂CO₃ / dioxane

2: H₂; AcOH / Pd/C

3: aq. NaHCO₃ / dioxane

4: H₂N-NH₂*AcOH / methanol / 50 °C

5: DIEA; EDC; HOBt / CHCl₃

6: H₂ / 10 percent Pd/C / methanol

7: DIEA; EDC; HOBt / dimethylformamide

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

9: DIEA; EDC; HOBt / dimethylformamide

10: 95 percent aq. TFA / 0 - 20 °C

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

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

Reference yield:

2-Amino-3-(3-cyano-phenyl)-propionic acid methyl ester (164648-62-8) → 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 (325773-94-2)

Guidance literature:

Multi-step reaction with 9 steps

1: aq. Na₂CO₃ / dioxane

2: H₂; AcOH / Pd/C

3: aq. NaHCO₃ / dioxane

4: H₂N-NH₂*AcOH / methanol / 50 °C

5: DIEA; EDC; HOBt / CHCl₃

6: H₂ / 10 percent Pd/C / methanol

7: DIEA; EDC; HOBt / dimethylformamide

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

9: DIEA; EDC; HOBt / dimethylformamide

With 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:

methanol

(+/-)-3-cyanophenylalanine

Downstream raw materials:

3-(3-cyano-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester

2-amino-3-[3-(tert-butoxycarbonylamino-methyl)-phenyl]-propionic acid methyl ester

3-(3-aminomethyl-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester

2-(2-amino-acetylamino)-3-[3-(tert-butoxycarbonylamino-methyl)-phenyl]-propionic acid methyl ester

Refernces