[2-{(R)-[tert-butoxycarbonylamino-(3,5-dichloro-4-methoxyphenyl)acetyl]methylamino}-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester

Base Information

• Chemical Name: [2-{(R)-[tert-butoxycarbonylamino-(3,5-dichloro-4-methoxyphenyl)acetyl]methylamino}-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester
• CAS No.: 193074-02-1
• Molecular Formula: C₃₄H₃₇Cl₂FN₄O₁₀
• Molecular Weight: 751.593
• Mol file: 193074-02-1.mol

Synonyms:[2-{(R)-[tert-butoxycarbonylamino-(3,5-dichloro-4-methoxyphenyl)acetyl]methylamino}-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester

Chemical Property of [2-{(R)-[tert-butoxycarbonylamino-(3,5-dichloro-4-methoxyphenyl)acetyl]methylamino}-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [2-{(R)-[tert-butoxycarbonylamino-(3,5-dichloro-4-methoxyphenyl)acetyl]methylamino}-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester

There total 21 articles about [2-{(R)-[tert-butoxycarbonylamino-(3,5-dichloro-4-methoxyphenyl)acetyl]methylamino}-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic 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: 65.0%

[3-(4-fluoro-3-nitrophenyl)-(2S)-2-methylaminopropionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester (193073-99-3) + N-(tert-butoxycarbonyl)-(R)-(3,5-dichloro-4-methoxy)phenylglycine (193073-75-5) → [2-{(R)-[tert-butoxycarbonylamino-(3,5-dichloro-4-methoxyphenyl)acetyl]methylamino}-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester (193074-02-1)

Guidance literature:

With bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane; at 0 ℃;

DOI:10.1016/S0040-4039(97)00938-6

Reference yield: 65.0%

[3-(4-fluoro-3-nitrophenyl)-(2S)-2-methylaminopropionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester (193073-99-3) + N-(tert-butoxycarbonyl)-(R)-(3,5-dichloro-4-methoxy)phenylglycine (193073-75-5) → [2-{(R)-[tert-butoxycarbonylamino-(3,5-dichloro-4-methoxyphenyl)acetyl]methylamino}-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester (193074-02-1) + (R)-[(S)-2-{[(S)-2-tert-Butoxycarbonylamino-2-(3,5-dichloro-4-methoxy-phenyl)-acetyl]-methyl-amino}-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-(4-methoxy-phenyl)-acetic acid methyl ester

Guidance literature:

With bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane; at 20 ℃; for 4h;

DOI:10.3987/COM-99-8514

Reference yield:

4-fluoro-3-nitrobenzaldehyde (42564-51-2) → [2-{(R)-[tert-butoxycarbonylamino-(3,5-dichloro-4-methoxyphenyl)acetyl]methylamino}-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester (193074-02-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 98 percent / NaBH₄ / methanol

2: 82 percent / PBr₃ / toluene

3: 54 percent / n-C₄H₉Li; CuCN / tetrahydrofuran / 20 °C

4: 65 percent / TFA / acetonitrile; H₂O

5: 54 percent / N(C₂H₅)3 / tetrahydrofuran / 16 h / 20 °C

6: 83 percent / Ag₂O / dimethylformamide / 60 h / 60 °C

7: 90 percent / K₂CO₃; H₂O / methanol / 6 h / 20 °C

8: 92 percent / N(C₂H₅)3; EDC; HOBT / CH₂Cl₂ / 2 h / 20 °C

9: 94 percent / NaI; TMSCl / CHCl₃ / 0.17 h / 20 °C

10: 65 percent / bromo-tris(pyrrolidino)phosphonium hexafluorophosphate / CH₂Cl₂ / 4 h / 20 °C

With sodium tetrahydroborate; n-butyllithium; chloro-trimethyl-silane; water; phosphorus tribromide; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; trifluoroacetic acid; sodium iodide; silver(l) oxide; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Reduction / 2: Bromination / 3: Alkylation / 4: Hydrolysis / 5: Acylation / 6: Methylation / 7: Hydrolysis / 8: Acylation / 9: deacylation / 10: Acylation;

DOI:10.3987/COM-99-8514

upstream raw materials:

[3-(4-fluoro-3-nitrophenyl)-(2S)-2-methylaminopropionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester

N-(tert-butoxycarbonyl)-(R)-(3,5-dichloro-4-methoxy)phenylglycine

di-tert-butyl dicarbonate

(4-fluoro-3-nitrophenyl)methanol

Downstream raw materials:

[2-{(R)-[amino-(3,5-dichloro-4-methoxyphenyl)acetyl]methylamino}-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester

[2-({(R)-(3,5-dichloro-4-methoxyphenyl)-[2-(3-hydroxyphenyl)acetylamino]acetyl}methylamino)-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester