trans-2-butoxycarbonylamino-3-{2-[3-(4-cyanophenyl)-4-hydroxy-4,5-dihydroisoxazol-5-yl]acetylamino}propionic acid methyl ester

Base Information

• Chemical Name: trans-2-butoxycarbonylamino-3-{2-[3-(4-cyanophenyl)-4-hydroxy-4,5-dihydroisoxazol-5-yl]acetylamino}propionic acid methyl ester
• CAS No.: 313342-91-5
• Molecular Formula: C₂₁H₂₆N₄O₇
• Molecular Weight: 446.46
• Mol file: 313342-91-5.mol

Synonyms:trans-2-butoxycarbonylamino-3-{2-[3-(4-cyanophenyl)-4-hydroxy-4,5-dihydroisoxazol-5-yl]acetylamino}propionic acid methyl ester

Chemical Property of trans-2-butoxycarbonylamino-3-{2-[3-(4-cyanophenyl)-4-hydroxy-4,5-dihydroisoxazol-5-yl]acetylamino}propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-2-butoxycarbonylamino-3-{2-[3-(4-cyanophenyl)-4-hydroxy-4,5-dihydroisoxazol-5-yl]acetylamino}propionic acid methyl ester

There total 4 articles about trans-2-butoxycarbonylamino-3-{2-[3-(4-cyanophenyl)-4-hydroxy-4,5-dihydroisoxazol-5-yl]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:

4-acetoxy-3-(4-cyanophenyl)-5-(2-hydroxyethyl)-4,5-dihydroisoxazole → trans-2-butoxycarbonylamino-3-{2-[3-(4-cyanophenyl)-4-hydroxy-4,5-dihydroisoxazol-5-yl]acetylamino}propionic acid methyl ester (313342-91-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / PDC / dimethylformamide / 15 h / 20 °C

2: 84 percent / DCC; 1-hydroxybenzotriazole hydrate; Et₃N / dimethylformamide / 20 °C

3: CHIRALPAK AD column / methanol; H₂O

With dipyridinium dichromate; CHIRALPAK AD column; 1-hydroxybenzotriazol-hydrate; triethylamine; dicyclohexyl-carbodiimide; In methanol; water; N,N-dimethyl-formamide; 1: Oxidation / 2: Acylation / 3: Hydrolysis;

DOI:10.1021/jo000755o

Reference yield:

4-acetoxy-3-(4-cyanophenyl)-4,5-dihydroisoxazol-5-ylacetic acid → trans-2-butoxycarbonylamino-3-{2-[3-(4-cyanophenyl)-4-hydroxy-4,5-dihydroisoxazol-5-yl]acetylamino}propionic acid methyl ester (313342-91-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / DCC; 1-hydroxybenzotriazole hydrate; Et₃N / dimethylformamide / 20 °C

2: CHIRALPAK AD column / methanol; H₂O

With CHIRALPAK AD column; 1-hydroxybenzotriazol-hydrate; triethylamine; dicyclohexyl-carbodiimide; In methanol; water; N,N-dimethyl-formamide; 1: Acylation / 2: Hydrolysis;

DOI:10.1021/jo000755o

Reference yield:

4-{(4S,5R)-4-Hydroxy-5-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-4,5-dihydro-isoxazol-3-yl}-benzonitrile → trans-2-butoxycarbonylamino-3-{2-[3-(4-cyanophenyl)-4-hydroxy-4,5-dihydroisoxazol-5-yl]acetylamino}propionic acid methyl ester (313342-91-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.30 g / pyridine / 8 h / 20 °C

2: 398 mg / AcOH / tetrahydrofuran / 3 h / 50 - 55 °C

3: 76 percent / PDC / dimethylformamide / 15 h / 20 °C

4: 84 percent / DCC; 1-hydroxybenzotriazole hydrate; Et₃N / dimethylformamide / 20 °C

5: CHIRALPAK AD column / methanol; H₂O

With pyridine; dipyridinium dichromate; CHIRALPAK AD column; acetic acid; 1-hydroxybenzotriazol-hydrate; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; 1: Acetylation / 2: ether cleavage / 3: Oxidation / 4: Acylation / 5: Hydrolysis;

DOI:10.1021/jo000755o