(S)-1-{(R)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-4-methyl-pentanoyloxy]-3-phenyl-propionyl}-piperidine-2-carboxylic acid (R)-1-carboxy-ethyl ester

Base Information

• Chemical Name: (S)-1-{(R)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-4-methyl-pentanoyloxy]-3-phenyl-propionyl}-piperidine-2-carboxylic acid (R)-1-carboxy-ethyl ester
• CAS No.: 187851-84-9
• Molecular Formula: C₃₀H₄₄N₂O₉
• Molecular Weight: 576.687
• Mol file: 187851-84-9.mol

Synonyms:(S)-1-{(R)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-4-methyl-pentanoyloxy]-3-phenyl-propionyl}-piperidine-2-carboxylic acid (R)-1-carboxy-ethyl ester

Chemical Property of (S)-1-{(R)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-4-methyl-pentanoyloxy]-3-phenyl-propionyl}-piperidine-2-carboxylic acid (R)-1-carboxy-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-{(R)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-4-methyl-pentanoyloxy]-3-phenyl-propionyl}-piperidine-2-carboxylic acid (R)-1-carboxy-ethyl ester

There total 4 articles about (S)-1-{(R)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-4-methyl-pentanoyloxy]-3-phenyl-propionyl}-piperidine-2-carboxylic acid (R)-1-carboxy-ethyl 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: 98.0%

(S)-1-{(R)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-4-methyl-pentanoyloxy]-3-phenyl-propionyl}-piperidine-2-carboxylic acid (R)-1-benzyloxycarbonyl-ethyl ester (187851-83-8) → (S)-1-{(R)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-4-methyl-pentanoyloxy]-3-phenyl-propionyl}-piperidine-2-carboxylic acid (R)-1-carboxy-ethyl ester (187851-84-9)

Guidance literature:

With hydrogen; 10% palladium on active carbon; In ethanol; for 17h; under 2068.59 Torr;

DOI:10.1016/S0960-894X(01)00748-X

Reference yield:

(S)-(-)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid (26250-84-0) → (S)-1-{(R)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-4-methyl-pentanoyloxy]-3-phenyl-propionyl}-piperidine-2-carboxylic acid (R)-1-carboxy-ethyl ester (187851-84-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / triphenylphosphine; diethyl azodicarboxylate / diethyl ether / 1 h / 20 °C

2: TFA / CH₂Cl₂ / 1.5 h

3: 4 g / diisopropylcarbodiimide; dimethylaminopyridine / CH₂Cl₂ / 16 h / 20 °C

4: 98 percent / H₂ / 10 percent Pd/C / ethanol / 17 h / 2068.59 Torr

With dmap; hydrogen; triphenylphosphine; trifluoroacetic acid; diisopropyl-carbodiimide; diethylazodicarboxylate; 10% palladium on active carbon; In diethyl ether; ethanol; dichloromethane;

DOI:10.1016/S0960-894X(01)00748-X

Reference yield:

(S)-Piperidine-1,2-dicarboxylic acid 2-((R)-1-benzyloxycarbonyl-ethyl) ester 1-tert-butyl ester (187851-81-6) → (S)-1-{(R)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-4-methyl-pentanoyloxy]-3-phenyl-propionyl}-piperidine-2-carboxylic acid (R)-1-carboxy-ethyl ester (187851-84-9)

Guidance literature:

Multi-step reaction with 3 steps

1: TFA / CH₂Cl₂ / 1.5 h

2: 4 g / diisopropylcarbodiimide; dimethylaminopyridine / CH₂Cl₂ / 16 h / 20 °C

3: 98 percent / H₂ / 10 percent Pd/C / ethanol / 17 h / 2068.59 Torr

With dmap; hydrogen; trifluoroacetic acid; diisopropyl-carbodiimide; 10% palladium on active carbon; In ethanol; dichloromethane;

DOI:10.1016/S0960-894X(01)00748-X

upstream raw materials:

(S)-1-{(R)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-4-methyl-pentanoyloxy]-3-phenyl-propionyl}-piperidine-2-carboxylic acid (R)-1-benzyloxycarbonyl-ethyl ester

(S)-(-)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid

benzyl L-pipecolyl-D-lactate

(S)-Piperidine-1,2-dicarboxylic acid 2-((R)-1-benzyloxycarbonyl-ethyl) ester 1-tert-butyl ester