1-[2-(tert-butoxycarbonyl-tert-butoxycarbonylmethyl-amino)-3-cyclohexyl-propionyl]-2,5-dihydro-1H-pyrrole-2-carboxylic acid

Base Information

• Chemical Name: 1-[2-(tert-butoxycarbonyl-tert-butoxycarbonylmethyl-amino)-3-cyclohexyl-propionyl]-2,5-dihydro-1H-pyrrole-2-carboxylic acid
• CAS No.: 203792-23-8
• Molecular Formula: C₂₅H₄₀N₂O₇
• Molecular Weight: 480.602
• Mol file: 203792-23-8.mol

Synonyms:1-[2-(tert-butoxycarbonyl-tert-butoxycarbonylmethyl-amino)-3-cyclohexyl-propionyl]-2,5-dihydro-1H-pyrrole-2-carboxylic acid

Chemical Property of 1-[2-(tert-butoxycarbonyl-tert-butoxycarbonylmethyl-amino)-3-cyclohexyl-propionyl]-2,5-dihydro-1H-pyrrole-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[2-(tert-butoxycarbonyl-tert-butoxycarbonylmethyl-amino)-3-cyclohexyl-propionyl]-2,5-dihydro-1H-pyrrole-2-carboxylic acid

There total 9 articles about 1-[2-(tert-butoxycarbonyl-tert-butoxycarbonylmethyl-amino)-3-cyclohexyl-propionyl]-2,5-dihydro-1H-pyrrole-2-carboxylic 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: 94.0%

C26H42N2O7 (203792-22-7) → 1-[2-(tert-butoxycarbonyl-tert-butoxycarbonylmethyl-amino)-3-cyclohexyl-propionyl]-2,5-dihydro-1H-pyrrole-2-carboxylic acid (203792-23-8)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 20 ℃; for 2h;

DOI:10.1016/j.bmcl.2006.02.040

Reference yield:

1-[2-(tert-butoxycarbonyl-tert-butoxycarbonylmethyl-amino)-3-cyclohexyl-propionyl]-2,5-dihydro-1H-pyrrole-2-carboxylic acid benzyl ester → 1-[2-(tert-butoxycarbonyl-tert-butoxycarbonylmethyl-amino)-3-cyclohexyl-propionyl]-2,5-dihydro-1H-pyrrole-2-carboxylic acid (203792-23-8)

Guidance literature:

With hydrogen; 10percent Pd/C; In methanol; at 20 ℃; atmospheric pressure;

DOI:10.1021/jm011110z

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 1-[2-(tert-butoxycarbonyl-tert-butoxycarbonylmethyl-amino)-3-cyclohexyl-propionyl]-2,5-dihydro-1H-pyrrole-2-carboxylic acid (203792-23-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 70 percent / DiPEA / dimethylformamide / 16 h / 20 °C / pH 8.5

2: 93 percent / aq. NaOH / dioxane / 6 h / 20 °C / pH 12

3: HOBt; DCCI; Et₃N / dimethylformamide / 0 - 20 °C

4: H₂ / 10percent Pd/C / methanol / 20 °C / atmospheric pressure

With sodium hydroxide; hydrogen; benzotriazol-1-ol; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; 10percent Pd/C; In 1,4-dioxane; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm011110z

upstream raw materials:

di-tert-butyl dicarbonate

D-cyclohexylalanine hydrochloride

methyl (R)-2-amino-3-cyclohexylpropanoate hydrochloride

N-(tert-butyloxycarbonylmethyl)-D-Cha-OMe

Downstream raw materials:

[tert-butoxycarbonyl-(2-{2-[(5-carbamimidoyl-1-methyl-1H-pyrrol-2-ylmethyl)-carbamoyl]-2,5-dihydro-pyrrol-1-yl}-1-cyclohexylmethyl-2-oxo-ethyl)-amino]-acetic acid tert-butyl ester

C₂₉H₄₂N₆O₇

C₃₁H₄₄N₄O₆S

tert-butyl {(tert-butoxycarbonyl)[(1R)-2-[(2S)-2-({[(6-cyano-3-pyridinyl)methyl]amino}carbonyl)-2,5-dihydro-1H-pyrrol-1-yl]-1-(cyclohexylmethyl)-2-oxoethyl]amino}acetate