3-Piperidinecarboxylic acid, 1-((2R)-2-((2-amino-2-methyl-1-oxopropyl)amino)-3-(1H-indol-3-yl)-1-oxopropyl)-3-(phenylmethyl)-, ethyl ester, (3S)-

Base Information

• Chemical Name: 3-Piperidinecarboxylic acid, 1-((2R)-2-((2-amino-2-methyl-1-oxopropyl)amino)-3-(1H-indol-3-yl)-1-oxopropyl)-3-(phenylmethyl)-, ethyl ester, (3S)-
• CAS No.: 170842-48-5
• Molecular Formula: C30H38N4O4
• UNII: KA8UGJ5WPL
• Nikkaji Number: J997.962J
• Pharos Ligand ID: YZ33NY9UYJVG
• ChEMBL ID: CHEMBL79263
• Mol file: 170842-48-5.mol

Synonyms:1-(2(R)-(2-amino-2-methylpropionyl-amino)-3-(1H-indol-3-yl)propionyl)-3-benzylpiperidine-3(S)-carboxylic acid ethy ester;L 163540;L-163540

Chemical Property of 3-Piperidinecarboxylic acid, 1-((2R)-2-((2-amino-2-methyl-1-oxopropyl)amino)-3-(1H-indol-3-yl)-1-oxopropyl)-3-(phenylmethyl)-, ethyl ester, (3S)-

Chemical Property:

• XLogP3: 3.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 518.28930571
• Heavy Atom Count: 38
• Complexity: 842

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C1(CCCN(C1)C(=O)C(CC2=CNC3=CC=CC=C32)NC(=O)C(C)(C)N)CC4=CC=CC=C4
• Isomeric SMILES: CCOC(=O)[C@@]1(CCCN(C1)C(=O)[C@@H](CC2=CNC3=CC=CC=C32)NC(=O)C(C)(C)N)CC4=CC=CC=C4

Technology Process of 3-Piperidinecarboxylic acid, 1-((2R)-2-((2-amino-2-methyl-1-oxopropyl)amino)-3-(1H-indol-3-yl)-1-oxopropyl)-3-(phenylmethyl)-, ethyl ester, (3S)-

There total 13 articles about 3-Piperidinecarboxylic acid, 1-((2R)-2-((2-amino-2-methyl-1-oxopropyl)amino)-3-(1H-indol-3-yl)-1-oxopropyl)-3-(phenylmethyl)-, ethyl ester, (3S)- 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:

diethyl 2-benzyl-2-(2-cyanoethyl)malonate (10444-15-2) → L-163,540 (170842-48-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 70 percent / H₂, aq. HCl / Pd(OH)2 / ethanol / 22 h / 50 °C / 2172.02 Torr

2: 89 percent / Et₃N / CH₂Cl₂ / 2 h / 25 °C

3: phosphate buffer, porcine liver esterase / H₂O / 27 h / 37 °C

4: TFA / CH₂Cl₂ / 1.5 h / 40 °C

5: DCC, DIEA, HOBT, DMAP / CH₂Cl₂ / 20 h / 25 °C

6: Lawesson's reagent / toluene / 2 h / 110 °C

7: 100 mg / NaBH₄, Raney Ni / tetrahydrofuran; ethanol; H₂O / 0.25 h

8: DCC, HOBt / ethyl acetate / 16 h / 22 °C

9: 3.41 kg / HCl / ethanol / 1 h / 60 °C

10: DCC, HOBt, DIEA / ethyl acetate / 1 h / 26 °C

11: HCl / ethanol / 2 h / 25 °C

With Lawessons reagent; hydrogenchloride; porcine liver esterase; dmap; sodium tetrahydroborate; phosphate buffer; hydrogen; nickel; benzotriazol-1-ol; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; toluene;

DOI:10.1021/jo980990v

Reference yield:

diethyl 2-benzylmalonate (607-81-8) → L-163,540 (170842-48-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 99 percent / EtONa, MTBE / ethanol / 1 h / 40 °C

2: 70 percent / H₂, aq. HCl / Pd(OH)2 / ethanol / 22 h / 50 °C / 2172.02 Torr

3: 89 percent / Et₃N / CH₂Cl₂ / 2 h / 25 °C

4: phosphate buffer, porcine liver esterase / H₂O / 27 h / 37 °C

5: TFA / CH₂Cl₂ / 1.5 h / 40 °C

6: DCC, DIEA, HOBT, DMAP / CH₂Cl₂ / 20 h / 25 °C

7: Lawesson's reagent / toluene / 2 h / 110 °C

8: 100 mg / NaBH₄, Raney Ni / tetrahydrofuran; ethanol; H₂O / 0.25 h

9: DCC, HOBt / ethyl acetate / 16 h / 22 °C

10: 3.41 kg / HCl / ethanol / 1 h / 60 °C

11: DCC, HOBt, DIEA / ethyl acetate / 1 h / 26 °C

12: HCl / ethanol / 2 h / 25 °C

With Lawessons reagent; hydrogenchloride; porcine liver esterase; dmap; sodium tetrahydroborate; phosphate buffer; tert-butyl methyl ether; hydrogen; sodium ethanolate; nickel; benzotriazol-1-ol; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; toluene;

DOI:10.1021/jo980990v

Reference yield:

(S)-3-Benzyl-1-[(R)-2-(2-tert-butoxycarbonylamino-2-methyl-propionylamino)-3-(1H-indol-3-yl)-propionyl]-piperidine-3-carboxylic acid ethyl ester (170842-83-8) → L-163,540 (170842-48-5)

Guidance literature:

With hydrogenchloride; In ethanol; at 25 ℃; for 2h;

DOI:10.1021/jo980990v

upstream raw materials:

(S)-3-Benzyl-1-[(R)-2-(2-tert-butoxycarbonylamino-2-methyl-propionylamino)-3-(1H-indol-3-yl)-propionyl]-piperidine-3-carboxylic acid ethyl ester

diethyl 2-benzyl-2-(2-cyanoethyl)malonate

diethyl 2-benzylmalonate

(S)-3-carbethoxy-3-benzylpiperidine