[(2S)-2-(tert-butoxycarbonylmethylamino)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)methyl ester

Base Information

• Chemical Name: [(2S)-2-(tert-butoxycarbonylmethylamino)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)methyl ester
• CAS No.: 193073-96-0
• Molecular Formula: C₂₅H₃₀FN₃O₈
• Molecular Weight: 519.527
• Mol file: 193073-96-0.mol

Synonyms:[(2S)-2-(tert-butoxycarbonylmethylamino)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)methyl ester

Chemical Property of [(2S)-2-(tert-butoxycarbonylmethylamino)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2S)-2-(tert-butoxycarbonylmethylamino)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)methyl ester

There total 13 articles about [(2S)-2-(tert-butoxycarbonylmethylamino)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)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: 92.0%

(R)-Amino-(4-methoxy-phenyl)-acetic acid methyl ester; hydrochloride + (S)-N-(tert-butoxycarbonyl)-N-methyl-(S)-(4-fluoro-3-nitro)phenylalanine (193073-38-0) → [(2S)-2-(tert-butoxycarbonylmethylamino)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)methyl ester (193073-96-0) + (S)-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-(4-methoxy-phenyl)-acetic acid methyl ester

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.3987/COM-99-8514

Reference yield: 92.0%

methyl 4-methoxyphenyl-D-phenylglycinate (78307-39-8) + (S)-N-(tert-butoxycarbonyl)-N-methyl-(S)-(4-fluoro-3-nitro)phenylalanine (193073-38-0) → [(2S)-2-(tert-butoxycarbonylmethylamino)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)methyl ester (193073-96-0)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane;

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

Reference yield:

4-fluoro-3-nitrobenzaldehyde (42564-51-2) → [(2S)-2-(tert-butoxycarbonylmethylamino)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)methyl ester (193073-96-0)

Guidance literature:

Multi-step reaction with 8 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

With sodium tetrahydroborate; n-butyllithium; water; phosphorus tribromide; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; silver(l) oxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Reduction / 2: Bromination / 3: Alkylation / 4: Hydrolysis / 5: Acylation / 6: Methylation / 7: Hydrolysis / 8: Acylation;

DOI:10.3987/COM-99-8514

upstream raw materials:

methyl 4-methoxyphenyl-D-phenylglycinate

(S)-N-(tert-butoxycarbonyl)-N-methyl-(S)-(4-fluoro-3-nitro)phenylalanine

(4-fluoro-3-nitrophenyl)methanol

4-fluoro-3-nitrobenzaldehyde

Downstream raw materials:

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

[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

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

(R)-[(S)-2-{[(S)-2-Amino-2-(3,5-dichloro-4-methoxy-phenyl)-acetyl]-methyl-amino}-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-(4-methoxy-phenyl)-acetic acid methyl ester