DMP 754

Base Information

• Chemical Name: DMP 754
• CAS No.: 170902-47-3
• Molecular Formula: C₂₁H₂₉N₅O₆
• Molecular Weight: 447.491
• Mol file: 170902-47-3.mol

Synonyms:L-Alanine,3-[[[(5R)-3-[4-(aminoiminomethyl)phenyl]-4,5-dihydro-5-isoxazolyl]acetyl]amino]-N-(butoxycarbonyl)-,methyl ester (9CI); L-Alanine,3-[[[3-[4-(aminoiminomethyl)phenyl]-4,5-dihydro-5-isoxazolyl]acetyl]amino]-N-(butoxycarbonyl)-,methyl ester, (R)-; DMP 755; Roxifiban

Chemical Property of DMP 754

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 172.17000
• Density: 1.35g/cm³
• LogP: 2.31820

Purity/Quality:

98%min ^*data from raw suppliers

ROXIFIBAN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Antithrombotic; fibrinogen receptor antagonist.

Technology Process of DMP 754

There total 13 articles about DMP 754 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: 85.0%

(2S)-2-butoxycarbonylamino-3-(2-{(5R)-3-[4-(N-hydroxycarbamimidoyl)-phenyl]-4,5-dihydro-isoxazol-5-yl}acetylamino)-propionic acid methyl ester → roxifiban (170902-47-3)

Guidance literature:

With hydrogen; acetic anhydride; acetic acid; palladium on activated charcoal; for 0.5h; under 775.743 Torr;

DOI:10.1080/00397910701575012

Reference yield: 61.0%

carbonochloridic acid, butyl ester (592-34-7) + methyl 3-[({3-[4-(aminomethyl)phenyl]-4,5-dihydro-5-isoxazolyl}acetyl)amino]-L-alanine bis(trifluoroacetate) → (S)-2-Butoxycarbonylamino-3-{2-[3-(4-carbamimidoyl-phenyl)-4,5-dihydro-isoxazol-5-yl]-acetylamino}-propionic acid methyl ester (190446-72-1,170902-47-3)

Guidance literature:

With sodium hydrogencarbonate; In acetonitrile; for 1h;

DOI:10.1021/jm960799i

Reference yield:

4-cyanobenzaldehyde oxime (52707-54-7,52707-59-2,64847-77-4) → (S)-2-Butoxycarbonylamino-3-{2-[3-(4-carbamimidoyl-phenyl)-4,5-dihydro-isoxazol-5-yl]-acetylamino}-propionic acid methyl ester (190446-72-1,170902-47-3)

Guidance literature:

Multi-step reaction with 9 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

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

upstream raw materials:

carbonochloridic acid, butyl 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

Refernces

• 1、 -. "Crystalline roxifiban". . . Retrieved 2008/06/13.