Benzoic acid (2R,4S)-4-((S)-1-allyloxycarbonyl-ethylcarbamoyl)-2-methyl-4-methylamino-butyl ester

Base Information

• Chemical Name: Benzoic acid (2R,4S)-4-((S)-1-allyloxycarbonyl-ethylcarbamoyl)-2-methyl-4-methylamino-butyl ester
• CAS No.: 855315-80-9
• Molecular Formula: C₂₀H₂₈N₂O₅
• Molecular Weight: 376.453
• Mol file: 855315-80-9.mol

Synonyms:Benzoic acid (2R,4S)-4-((S)-1-allyloxycarbonyl-ethylcarbamoyl)-2-methyl-4-methylamino-butyl ester

Chemical Property of Benzoic acid (2R,4S)-4-((S)-1-allyloxycarbonyl-ethylcarbamoyl)-2-methyl-4-methylamino-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,4S)-4-((S)-1-allyloxycarbonyl-ethylcarbamoyl)-2-methyl-4-methylamino-butyl ester

There total 4 articles about Benzoic acid (2R,4S)-4-((S)-1-allyloxycarbonyl-ethylcarbamoyl)-2-methyl-4-methylamino-butyl 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:

Benzoic acid (2R,4S)-4-((S)-1-allyloxycarbonyl-ethylcarbamoyl)-4-(tert-butoxycarbonyl-methyl-amino)-2-methyl-butyl ester (753487-77-3) → Benzoic acid (2R,4S)-4-((S)-1-allyloxycarbonyl-ethylcarbamoyl)-2-methyl-4-methylamino-butyl ester (855315-80-9)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/ol049065n

Reference yield:

Benzoic acid (2R,4S)-4-(tert-butoxycarbonyl-methyl-amino)-4-carboxy-2-methyl-butyl ester (753487-47-7) → Benzoic acid (2R,4S)-4-((S)-1-allyloxycarbonyl-ethylcarbamoyl)-2-methyl-4-methylamino-butyl ester (855315-80-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; diisopropylethylamine / CH₂Cl₂ / 0 - 20 °C

2: trifluoroacetic acid / 0 - 20 °C

With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/j.tet.2005.03.058

Reference yield:

(S)-4-((R)-3-Benzoyloxy-2-methyl-propyl)-5-oxo-oxazolidine-3-carboxylic acid tert-butyl ester (753487-53-5) → Benzoic acid (2R,4S)-4-((S)-1-allyloxycarbonyl-ethylcarbamoyl)-2-methyl-4-methylamino-butyl ester (855315-80-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Et₃SiH; TFA / 0 - 20 °C

1.2: 100 percent / NaHCO₃; NaOH / tetrahydrofuran; H₂O

2.1: 79 percent / HOBt; i-Pr₂NEt; EDCI / CH₂Cl₂ / 0 - 20 °C

3.1: TFA / CH₂Cl₂ / 2 h / 20 °C

With triethylsilane; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/ol049065n

upstream raw materials:

Benzoic acid (2R,4S)-4-((S)-1-allyloxycarbonyl-ethylcarbamoyl)-4-(tert-butoxycarbonyl-methyl-amino)-2-methyl-butyl ester

L-alanine allyl ester

Benzoic acid (2R,4S)-4-(tert-butoxycarbonyl-methyl-amino)-4-carboxy-2-methyl-butyl ester

(S)-4-((R)-3-Benzoyloxy-2-methyl-propyl)-5-oxo-oxazolidine-3-carboxylic acid tert-butyl ester

Downstream raw materials:

Benzoic acid (2R,4S)-4-((S)-1-allyloxycarbonyl-ethylcarbamoyl)-4-({(2S,3R)-2-amino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(1,1-dimethyl-allyl)-1H-indol-3-yl]-propionyl}-methyl-amino)-2-methyl-butyl ester

benzoic acid 4-({3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(1,1-dimethyl-allyl)-1H-indol-3-yl]-2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3,5-dimethyl-hex-4-enoylamino]-propionyl}-methyl-amino)-4-(1-carboxy-ethylcarbamoyl)-2-methyl-butyl ester

C₆₅H₈₃N₅O₁₀Si

benzoic acid 4-(1-allyloxycarbonyl-ethylcarbamoyl)-4-{[3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(1,1-dimethyl-allyl)-1H-indol-3-yl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionyl]-methyl-amino}-2-methyl-butyl ester