(R,S)-3-(4-{[N-(dimethylethoxycarbonyl)imino]aminomethyl}phenyl)-4,5-dihydro-5-isoxazoleacetic acid

Base Information

• Chemical Name: (R,S)-3-(4-{[N-(dimethylethoxycarbonyl)imino]aminomethyl}phenyl)-4,5-dihydro-5-isoxazoleacetic acid
• CAS No.: 170726-53-1
• Molecular Formula: C₁₇H₂₁N₃O₅
• Molecular Weight: 347.371
• Mol file: 170726-53-1.mol

Synonyms:(R,S)-3-(4-{[N-(dimethylethoxycarbonyl)imino]aminomethyl}phenyl)-4,5-dihydro-5-isoxazoleacetic acid

Chemical Property of (R,S)-3-(4-{[N-(dimethylethoxycarbonyl)imino]aminomethyl}phenyl)-4,5-dihydro-5-isoxazoleacetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R,S)-3-(4-{[N-(dimethylethoxycarbonyl)imino]aminomethyl}phenyl)-4,5-dihydro-5-isoxazoleacetic acid

There total 5 articles about (R,S)-3-(4-{[N-(dimethylethoxycarbonyl)imino]aminomethyl}phenyl)-4,5-dihydro-5-isoxazoleacetic 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: 97.0%

methyl (R,S)-3-(4-{[N-(dimethylethoxycarbonyl)imino]aminomethyl}phenyl)-4,5-dihydro-5-isoxazoleacetate (170726-52-0) → (R,S)-3-(4-{[N-(dimethylethoxycarbonyl)imino]aminomethyl}phenyl)-4,5-dihydro-5-isoxazoleacetic acid (170726-53-1)

Guidance literature:

With lithium hydroxide; In methanol; at 22 ℃; for 16h;

DOI:10.1021/jm960799i

Reference yield:

4-cyanobenzaldehyde oxime (52707-54-7,52707-59-2,64847-77-4) → (R,S)-3-(4-{[N-(dimethylethoxycarbonyl)imino]aminomethyl}phenyl)-4,5-dihydro-5-isoxazoleacetic acid (170726-53-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 34 percent / aq. NaOCl / tetrahydrofuran / Ambient temperature

2: 73 percent / HCl / 24 h / Ambient temperature

3: NH₃ / methanol / 14 h / Ambient temperature

4: 75 percent / Et₃N / dimethylformamide / 16 h / 22 °C

5: 97 percent / aq. LiOH*H₂O / methanol / 16 h / 22 °C

With hydrogenchloride; lithium hydroxide; sodium hypochlorite; ammonia; triethylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm960799i

Reference yield:

[3-(4-cyano-phenyl)-4,5-dihydro-isoxazol-5-yl]-acetic acid (170229-13-7) → (R,S)-3-(4-{[N-(dimethylethoxycarbonyl)imino]aminomethyl}phenyl)-4,5-dihydro-5-isoxazoleacetic acid (170726-53-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 73 percent / HCl / 24 h / Ambient temperature

2: NH₃ / methanol / 14 h / Ambient temperature

3: 75 percent / Et₃N / dimethylformamide / 16 h / 22 °C

4: 97 percent / aq. LiOH*H₂O / methanol / 16 h / 22 °C

With hydrogenchloride; lithium hydroxide; ammonia; triethylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm960799i

upstream raw materials:

methyl (R,S)-3-(4-{[N-(dimethylethoxycarbonyl)imino]aminomethyl}phenyl)-4,5-dihydro-5-isoxazoleacetate

4-cyanobenzaldehyde oxime

[3-(4-cyano-phenyl)-4,5-dihydro-isoxazol-5-yl]-acetic acid

Downstream raw materials:

(R)-3-{2-[3-(4-{Amino-[(E)-tert-butoxycarbonylimino]-methyl}-phenyl)-4,5-dihydro-isoxazol-5-yl]-acetylamino}-4-phenyl-butyric acid methyl ester

(S)-2-Benzyloxycarbonylamino-3-{2-[3-(4-carbamimidoyl-phenyl)-4,5-dihydro-isoxazol-5-yl]-acetylamino}-propionic acid methyl ester

Refernces