<10R-(10α,14β,17α)>-10-(1H-indol-3-ylmethyl)-8,11,16,19-tetraoxo-14-phenyl-7,9,12,15,18-pentaazaspiro<5,13>nonadecane-17-acetic acid

Base Information

• Chemical Name: <10R-(10α,14β,17α)>-10-(1H-indol-3-ylmethyl)-8,11,16,19-tetraoxo-14-phenyl-7,9,12,15,18-pentaazaspiro<5,13>nonadecane-17-acetic acid
• CAS No.: 144876-95-9
• Molecular Formula: C₃₁H₃₆N₆O₆
• Molecular Weight: 588.663
• Mol file: 144876-95-9.mol

Synonyms:<10R-(10α,14β,17α)>-10-(1H-indol-3-ylmethyl)-8,11,16,19-tetraoxo-14-phenyl-7,9,12,15,18-pentaazaspiro<5,13>nonadecane-17-acetic acid

Chemical Property of <10R-(10α,14β,17α)>-10-(1H-indol-3-ylmethyl)-8,11,16,19-tetraoxo-14-phenyl-7,9,12,15,18-pentaazaspiro<5,13>nonadecane-17-acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <10R-(10α,14β,17α)>-10-(1H-indol-3-ylmethyl)-8,11,16,19-tetraoxo-14-phenyl-7,9,12,15,18-pentaazaspiro<5,13>nonadecane-17-acetic acid

There total 13 articles about <10R-(10α,14β,17α)>-10-(1H-indol-3-ylmethyl)-8,11,16,19-tetraoxo-14-phenyl-7,9,12,15,18-pentaazaspiro<5,13>nonadecane-17-acetic 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: 71.0%

methyl <10R-(10α,14β,17α)>-10-(1H-indol-3-ylmethyl)-8,11,16,19-tetraoxo-14-phenyl-7,9,12,15,18-petaazaspiro<5,13>nonadecane-17-acetate (144876-92-6) → <10R-(10α,14β,17α)>-10-(1H-indol-3-ylmethyl)-8,11,16,19-tetraoxo-14-phenyl-7,9,12,15,18-pentaazaspiro<5,13>nonadecane-17-acetic acid (144876-95-9)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 25 ℃; for 17h;

DOI:10.1016/S0040-4020(01)86596-0

Reference yield:

1-{[(benzyloxy)carbonyl]amino}cyclohexanecarboxylic acid (17191-43-4) → <10R-(10α,14β,17α)>-10-(1H-indol-3-ylmethyl)-8,11,16,19-tetraoxo-14-phenyl-7,9,12,15,18-pentaazaspiro<5,13>nonadecane-17-acetic acid (144876-95-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 68 percent / dicyclohexylcarbodiimide, 4-dimethylaminopyridine / acetonitrile; dimethylformamide / 24 h / Ambient temperature

2: 99 percent / H₂ / 20percent Pd(OH)2/C / propan-2-ol / 17 h / 25 °C / 2327.2 Torr

3: 96 percent / NEt₃ / tetrahydrofuran / 25 °C

4: 81 percent / toluene; tetrahydrofuran / 16 h / 80 - 100 °C

5: 95 percent / TFA / CH₂Cl₂ / 17 h / 25 °C

6: 80 percent / BOP, i-Pr₂NEt / dimethylformamide / 12 h / 25 °C

7: 1.1 g / H₂ / 20percent Pd(OH)2/C / petroleum ether / 12 h / 25 °C / 2327.2 Torr

8: 63 percent / DPPA, NaHCO₃ / dimethylformamide / 72 h / 25 °C

9: 71 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 17 h / 25 °C

With dmap; lithium hydroxide; diphenyl-phosphinic acid; hydrogen; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; acetonitrile; Petroleum ether;

DOI:10.1016/S0040-4020(01)86596-0

Reference yield:

((S)-2-Amino-1-phenyl-ethyl)-carbamic acid benzyl ester (130406-36-9,142854-51-1) → <10R-(10α,14β,17α)>-10-(1H-indol-3-ylmethyl)-8,11,16,19-tetraoxo-14-phenyl-7,9,12,15,18-pentaazaspiro<5,13>nonadecane-17-acetic acid (144876-95-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 1) hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide / 1) THF, EtOAc, 25 deg C, 2 h, 2) 25 deg C, 17 h

2: 89 percent / piperidine / dimethylformamide / 17 h / 0 °C

3: 81 percent / toluene; tetrahydrofuran / 16 h / 80 - 100 °C

4: 95 percent / TFA / CH₂Cl₂ / 17 h / 25 °C

5: 80 percent / BOP, i-Pr₂NEt / dimethylformamide / 12 h / 25 °C

6: 1.1 g / H₂ / 20percent Pd(OH)2/C / petroleum ether / 12 h / 25 °C / 2327.2 Torr

7: 63 percent / DPPA, NaHCO₃ / dimethylformamide / 72 h / 25 °C

8: 71 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 17 h / 25 °C

With piperidine; lithium hydroxide; diphenyl-phosphinic acid; hydrogen; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; Petroleum ether;

DOI:10.1016/S0040-4020(01)86596-0

upstream raw materials:

methyl <10R-(10α,14β,17α)>-10-(1H-indol-3-ylmethyl)-8,11,16,19-tetraoxo-14-phenyl-7,9,12,15,18-petaazaspiro<5,13>nonadecane-17-acetate

1-{[(benzyloxy)carbonyl]amino}cyclohexanecarboxylic acid

((S)-2-Amino-1-phenyl-ethyl)-carbamic acid benzyl ester

1-Amino-cyclohexanecarboxylic acid 2-trimethylsilanyl-ethyl ester