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

Base Information

• Chemical Name: 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
• CAS No.: 852714-76-2
• Molecular Formula: C₅₄H₇₅N₅O₁₀
• Molecular Weight: 954.217
• Mol file: 852714-76-2.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 1 articles about 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 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: 19.0%

(2S,3S)-3-(4-{bis[(tert-butyl)oxycarbonyl]methyl}-phenyl)-2-{[(tert-butyl)oxycarbonyl]methyl}-pent-4-enoic acid (641638-41-7) + N-{(2R)-2-[(5-methylindol-1-yl)methyl]pent-4-enyl}(2S)-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide (666259-67-2) → 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)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 - 50 ℃; for 72h;

DOI:10.1021/jm050059m

Reference yield: 81.0%

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) → 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)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 65 ℃; for 24h;

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

Guidance literature:

Multi-step reaction with 3 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

3: 19 percent / aq. LiOH / 4 h / 20 °C

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

DOI:10.1021/jm050059m

upstream raw materials:

(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

Downstream 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

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