3-[3-(4-Amidinophenyl)-4,5-dihydroisoxazol-5(R)-ylacetamido]-2(S)-(butoxycarbonylamino)propionic acid

Base Information

• Chemical Name: 3-[3-(4-Amidinophenyl)-4,5-dihydroisoxazol-5(R)-ylacetamido]-2(S)-(butoxycarbonylamino)propionic acid
• CAS No.: 170902-52-0
• Molecular Formula: C₂₀H₂₇N₅O₆
• Molecular Weight: 433.464
• Mol file: 170902-52-0.mol

Synonyms:L-Alanine,3-[[[(5R)-3-[4-(aminoiminomethyl)phenyl]-4,5-dihydro-5-isoxazolyl]acetyl]amino]-N-(butoxycarbonyl)-(9CI); L-Alanine,3-[[[3-[4-(aminoiminomethyl)phenyl]-4,5-dihydro-5-isoxazolyl]acetyl]amino]-N-(butoxycarbonyl)-,(R)-; XV 459

Chemical Property of 3-[3-(4-Amidinophenyl)-4,5-dihydroisoxazol-5(R)-ylacetamido]-2(S)-(butoxycarbonylamino)propionic acid

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.41g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-[3-(4-Amidinophenyl)-4,5-dihydroisoxazol-5(R)-ylacetamido]-2(S)-(butoxycarbonylamino)propionic acid

There total 10 articles about 3-[3-(4-Amidinophenyl)-4,5-dihydroisoxazol-5(R)-ylacetamido]-2(S)-(butoxycarbonylamino)propionic 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:

4-cyanobenzaldehyde oxime (52707-54-7,52707-59-2,64847-77-4) → 3-[({3-[4-(aminoiminomethyl)phenyl]-4,5-dihydro-5-isoxazolyl}acetyl)amino]-N-(butoxycarbonyl)-L-alanine (170902-52-0)

Guidance literature:

Multi-step reaction with 10 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

6: 89 percent / O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium tetrafkuoroborate, Et₃N / dimethylformamide / 16 h / Ambient temperature

7: 62 percent / 1,4-cyclohexadiene / 10percent Pd/C / methanol / 0.5 h / Ambient temperature

8: 94 percent / TFA / CH₂Cl₂ / 3 h / Ambient temperature

9: 61 percent / aq. NaHCO₃ / acetonitrile / 1 h

10: 1 N aq. LiOH / tetrahydrofuran / 1 h / Ambient temperature

With hydrogenchloride; lithium hydroxide; sodium hypochlorite; cyclohexa-1,4-diene; ammonia; sodium hydrogencarbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm960799i

Reference yield:

[3-(4-cyano-phenyl)-4,5-dihydro-isoxazol-5-yl]-acetic acid (170229-13-7) → 3-[({3-[4-(aminoiminomethyl)phenyl]-4,5-dihydro-5-isoxazolyl}acetyl)amino]-N-(butoxycarbonyl)-L-alanine (170902-52-0)

Guidance literature:

Multi-step reaction with 9 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

5: 89 percent / O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium tetrafkuoroborate, Et₃N / dimethylformamide / 16 h / Ambient temperature

6: 62 percent / 1,4-cyclohexadiene / 10percent Pd/C / methanol / 0.5 h / Ambient temperature

7: 94 percent / TFA / CH₂Cl₂ / 3 h / Ambient temperature

8: 61 percent / aq. NaHCO₃ / acetonitrile / 1 h

9: 1 N aq. LiOH / tetrahydrofuran / 1 h / Ambient temperature

With hydrogenchloride; lithium hydroxide; cyclohexa-1,4-diene; ammonia; sodium hydrogencarbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm960799i

Reference yield:

(R,S)-3-(4-{[N-(dimethylethoxycarbonyl)imino]aminomethyl}phenyl)-4,5-dihydro-5-isoxazoleacetic acid (170726-53-1) → 3-[({3-[4-(aminoiminomethyl)phenyl]-4,5-dihydro-5-isoxazolyl}acetyl)amino]-N-(butoxycarbonyl)-L-alanine (170902-52-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium tetrafkuoroborate, Et₃N / dimethylformamide / 16 h / Ambient temperature

2: 62 percent / 1,4-cyclohexadiene / 10percent Pd/C / methanol / 0.5 h / Ambient temperature

3: 94 percent / TFA / CH₂Cl₂ / 3 h / Ambient temperature

4: 61 percent / aq. NaHCO₃ / acetonitrile / 1 h

5: 1 N aq. LiOH / tetrahydrofuran / 1 h / Ambient temperature

With lithium hydroxide; cyclohexa-1,4-diene; sodium hydrogencarbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm960799i

upstream raw materials:

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

4-cyanobenzaldehyde oxime

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

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