2-{4-[(E)-(9S,10S,14R,18S)-18-Carbamoylmethyl-9-carboxymethyl-14-(5-methyl-indol-1-ylmethyl)-8,17,20-trioxo-7,16,19-triaza-spiro[5.14]icos-11-en-10-yl]-phenyl}-malonic acid

Base Information

• Chemical Name: 2-{4-[(E)-(9S,10S,14R,18S)-18-Carbamoylmethyl-9-carboxymethyl-14-(5-methyl-indol-1-ylmethyl)-8,17,20-trioxo-7,16,19-triaza-spiro[5.14]icos-11-en-10-yl]-phenyl}-malonic acid
• CAS No.: 852714-80-8
• Molecular Formula: C₄₀H₄₇N₅O₁₀
• Molecular Weight: 757.841
• Mol file: 852714-80-8.mol

Synonyms:2-{4-[(E)-(9S,10S,14R,18S)-18-Carbamoylmethyl-9-carboxymethyl-14-(5-methyl-indol-1-ylmethyl)-8,17,20-trioxo-7,16,19-triaza-spiro[5.14]icos-11-en-10-yl]-phenyl}-malonic acid

Chemical Property of 2-{4-[(E)-(9S,10S,14R,18S)-18-Carbamoylmethyl-9-carboxymethyl-14-(5-methyl-indol-1-ylmethyl)-8,17,20-trioxo-7,16,19-triaza-spiro[5.14]icos-11-en-10-yl]-phenyl}-malonic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{4-[(E)-(9S,10S,14R,18S)-18-Carbamoylmethyl-9-carboxymethyl-14-(5-methyl-indol-1-ylmethyl)-8,17,20-trioxo-7,16,19-triaza-spiro[5.14]icos-11-en-10-yl]-phenyl}-malonic acid

There total 4 articles about 2-{4-[(E)-(9S,10S,14R,18S)-18-Carbamoylmethyl-9-carboxymethyl-14-(5-methyl-indol-1-ylmethyl)-8,17,20-trioxo-7,16,19-triaza-spiro[5.14]icos-11-en-10-yl]-phenyl}-malonic 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: 38.0%

di-tert-butyl 2-[4-((9S,10S,18S,14R)-7,16,19-triaza-9-{[(tert-butyl)oxycarbonyl]methyl}-18-(carbamoylmethyl)-14-[(5-methylindolyl)methyl]-8,17,20-trioxospiro[5.14]icos-11-en-10-yl)phenyl]propane-1,3-dioate (852714-78-4) → 2-{4-[(E)-(9S,10S,14R,18S)-18-Carbamoylmethyl-9-carboxymethyl-14-(5-methyl-indol-1-ylmethyl)-8,17,20-trioxo-7,16,19-triaza-spiro[5.14]icos-11-en-10-yl]-phenyl}-malonic acid (852714-80-8)

Guidance literature:

With ethandithiol; trifluoroacetic acid; at 20 ℃; for 1.1h;

DOI:10.1021/jm050059m

Reference yield:

tert-butyl 2-[4-(1-{1-[N-({N-[1-(N-{(2R)-2-[(5-methylindolyl)methyl]-4-enyl}carbamoyl)-(1S)-2-carbamoylethyl]carbamoyl}cyclohexyl)carbamoyl]-(1S)-2-[(tert-butyl)oxycarbonyl]ethyl}-(1S)-prop-2-enyl)phenyl]propane-1,3-dioate (852714-76-2) → 2-{4-[(E)-(9S,10S,14R,18S)-18-Carbamoylmethyl-9-carboxymethyl-14-(5-methyl-indol-1-ylmethyl)-8,17,20-trioxo-7,16,19-triaza-spiro[5.14]icos-11-en-10-yl]-phenyl}-malonic acid (852714-80-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / [((PCy₃)(Im(Mes)2)Ru=CHPh)]Cl₂ / CH₂Cl₂ / 24 h / 65 °C

2: 38 percent / aq. TFA; ethanedithiol / 1.1 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; ethandithiol; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jm050059m

Reference yield:

N-{(2R)-2-[(5-methylindol-1-yl)methyl]pent-4-enyl}(2S)-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide (666259-67-2) → 2-{4-[(E)-(9S,10S,14R,18S)-18-Carbamoylmethyl-9-carboxymethyl-14-(5-methyl-indol-1-ylmethyl)-8,17,20-trioxo-7,16,19-triaza-spiro[5.14]icos-11-en-10-yl]-phenyl}-malonic acid (852714-80-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 19 percent / HOAt; EDCI*HCl / dimethylformamide / 72 h / 20 - 50 °C

2: 81 percent / [((PCy₃)(Im(Mes)2)Ru=CHPh)]Cl₂ / CH₂Cl₂ / 24 h / 65 °C

3: 38 percent / aq. TFA; ethanedithiol / 1.1 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; ethandithiol; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm050059m

upstream raw materials:

di-tert-butyl 2-[4-((9S,10S,18S,14R)-7,16,19-triaza-9-{[(tert-butyl)oxycarbonyl]methyl}-18-(carbamoylmethyl)-14-[(5-methylindolyl)methyl]-8,17,20-trioxospiro[5.14]icos-11-en-10-yl)phenyl]propane-1,3-dioate

tert-butyl 2-[4-(1-{1-[N-({N-[1-(N-{(2R)-2-[(5-methylindolyl)methyl]-4-enyl}carbamoyl)-(1S)-2-carbamoylethyl]carbamoyl}cyclohexyl)carbamoyl]-(1S)-2-[(tert-butyl)oxycarbonyl]ethyl}-(1S)-prop-2-enyl)phenyl]propane-1,3-dioate

(2S,3S)-3-(4-{bis[(tert-butyl)oxycarbonyl]methyl}-phenyl)-2-{[(tert-butyl)oxycarbonyl]methyl}-pent-4-enoic acid

N-{(2R)-2-[(5-methylindol-1-yl)methyl]pent-4-enyl}(2S)-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide