(2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoic acid

Base Information

• Chemical Name: (2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoic acid
• CAS No.: 728032-83-5
• Molecular Formula: C₂₄H₃₅ClN₂O₈
• Molecular Weight: 515.004
• Mol file: 728032-83-5.mol

Synonyms:(2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoic acid

Chemical Property of (2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoic acid

There total 5 articles about (2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoic 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: 98.0%

benzyl (2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoate (728032-81-3) → (2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoic acid (728032-83-5)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethyl acetate; for 2h;

DOI:10.1021/jm030555f

Reference yield:

(R)-2-hydroxy-4-methylpentanoic acid (20312-37-2,498-36-2) → (2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoic acid (728032-83-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 76 percent / K₂CO₃; tetrabutylammonium iodide / dimethylformamide / 1.5 h / 20 °C

2: 90 percent / DMAP; DCC / CH₂Cl₂ / 19.5 h / 0 - 20 °C

3: TFA / CH₂Cl₂ / 3.5 h / 20 °C

4: 0.63 g / HOBT; DIEA; DCC / tetrahydrofuran / 16.5 h / 0 - 20 °C

5: 98 percent / H₂ / Pd(OH)2 / ethyl acetate / 2 h

With dmap; hydrogen; tetra-(n-butyl)ammonium iodide; potassium carbonate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm030555f

Reference yield:

benzyl (R)-2-hydroxy-4-methylpentanoate (37755-48-9) → (2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoic acid (728032-83-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / DMAP; DCC / CH₂Cl₂ / 19.5 h / 0 - 20 °C

2: TFA / CH₂Cl₂ / 3.5 h / 20 °C

3: 0.63 g / HOBT; DIEA; DCC / tetrahydrofuran / 16.5 h / 0 - 20 °C

4: 98 percent / H₂ / Pd(OH)2 / ethyl acetate / 2 h

With dmap; hydrogen; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1021/jm030555f

upstream raw materials:

benzyl (2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoate

(R)-2-hydroxy-4-methylpentanoic acid

benzyl (R)-2-hydroxy-4-methylpentanoate

benzyl (2R)-2-(3-tert-butoxycarbonylaminopropionyloxy)-4-methylpentanoate

Downstream raw materials:

tert-butyl (5S,6R)-5-[(2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate

6-demethyldesepoxy-3-epicryptophycin-1