2(1H)-Isoquinolinecarboxylic acid, 3,4-dihydro-3-[[[(1S)-2-methoxy-2-oxo-1-(phenylmethyl)ethyl]amino]carb onyl]-, 1,1-dimethylethyl ester, (3R)-

Base Information

• Chemical Name: 2(1H)-Isoquinolinecarboxylic acid, 3,4-dihydro-3-[[[(1S)-2-methoxy-2-oxo-1-(phenylmethyl)ethyl]amino]carb onyl]-, 1,1-dimethylethyl ester, (3R)-
• CAS No.: 500213-40-1
• Molecular Formula: C25H30N2O5
• Molecular Weight: 438.524
• Mol file: 500213-40-1.mol

Synonyms:

Chemical Property of 2(1H)-Isoquinolinecarboxylic acid, 3,4-dihydro-3-[[[(1S)-2-methoxy-2-oxo-1-(phenylmethyl)ethyl]amino]carb onyl]-, 1,1-dimethylethyl ester, (3R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2(1H)-Isoquinolinecarboxylic acid, 3,4-dihydro-3-[[[(1S)-2-methoxy-2-oxo-1-(phenylmethyl)ethyl]amino]carb onyl]-, 1,1-dimethylethyl ester, (3R)-

There total 1 articles about 2(1H)-Isoquinolinecarboxylic acid, 3,4-dihydro-3-[[[(1S)-2-methoxy-2-oxo-1-(phenylmethyl)ethyl]amino]carb onyl]-, 1,1-dimethylethyl ester, (3R)- 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:

methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) + D-N-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinolinoline-3-carboxylic acid (78879-20-6,144069-68-1,115962-35-1) → 3-(1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (500213-40-1)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

DOI:10.1016/j.bmc.2006.03.028

Reference yield: 100.0%

3-(1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (500213-40-1) → (S)-3-Phenyl-2-[((R)-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl)-amino]-propionic acid methyl ester (617688-33-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; methoxybenzene;

DOI:10.1016/j.bmc.2006.03.028

Reference yield: 70.0%

3-(1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (500213-40-1) → C21H20N2O4

Guidance literature:

With pyridine; 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at 4 - 25 ℃; for 2.08333h; Inert atmosphere;

DOI:10.1021/ol502900j

upstream raw materials:

methyl (2S)-2-amino-3-phenylpropanoate

D-N-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinolinoline-3-carboxylic acid

Downstream raw materials:

(S)-3-Phenyl-2-[((R)-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl)-amino]-propionic acid methyl ester

C₆₆H₆₈N₈O₉

C₆₂H₆₆N₆O₁₁

(S)-2-({(R)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-3-phenyl-propionic acid methyl ester

Refernces

• 1、 Pan, Po-Shen,Curtis, Fiona A.,Carroll, Chris L.,Medina, Irene,Liotta, Lisa A.,Sharples, Gary J.,McAlpine, Shelli R.. "Novel antibiotics: C-2 symmetrical macrocycles inhibiting Holliday junction DNA binding by E. coli RuvC". . p. 4731 - 4739. Retrieved 2007/10/03.
• 2、 Liotta, Lisa A.,Medina, Irene,Robinson, Jennifer L.,Carroll, Chris L.,Pan, Po-Shen,Corral, Ricardo,Johnston, Jennifer V.C.,Cook, Kristina M.,Curtis, Fiona A.,Sharples, Gary J.,McAlpine, Shelli R.. "Novel antibiotics: Second generation macrocyclic peptides designed to trap Holliday junctions". . p. 8447 - 8450. Retrieved 2007/10/03.