3-Piperidinecarboxylic acid, 1-[N-[(1,1-dimethylethoxy)carbonyl]-2-methylalanyl-D-tryptophyl]-3-(phen ylmethyl)-, ethyl ester, (3S)-

Base Information

• Chemical Name: 3-Piperidinecarboxylic acid, 1-[N-[(1,1-dimethylethoxy)carbonyl]-2-methylalanyl-D-tryptophyl]-3-(phen ylmethyl)-, ethyl ester, (3S)-
• CAS No.: 170842-83-8
• Molecular Formula: C35H46N4O6
• Molecular Weight: 618.773
• Mol file: 170842-83-8.mol

Synonyms:

Chemical Property of 3-Piperidinecarboxylic acid, 1-[N-[(1,1-dimethylethoxy)carbonyl]-2-methylalanyl-D-tryptophyl]-3-(phen ylmethyl)-, ethyl ester, (3S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Piperidinecarboxylic acid, 1-[N-[(1,1-dimethylethoxy)carbonyl]-2-methylalanyl-D-tryptophyl]-3-(phen ylmethyl)-, ethyl ester, (3S)-

There total 16 articles about 3-Piperidinecarboxylic acid, 1-[N-[(1,1-dimethylethoxy)carbonyl]-2-methylalanyl-D-tryptophyl]-3-(phen ylmethyl)-, 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:

Boc-Aib-OH (30992-29-1) + (S)-1-[(R)-2-Amino-3-(1H-indol-3-yl)-propionyl]-3-benzyl-piperidine-3-carboxylic acid ethyl ester; hydrochloride → (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)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane;

DOI:10.1021/jm9800191

Reference yield:

diethyl 2-benzyl-2-(2-cyanoethyl)malonate (10444-15-2) → (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)

Guidance literature:

Multi-step reaction with 10 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

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) → (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)

Guidance literature:

Multi-step reaction with 11 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

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

upstream raw materials:

Boc-Aib-OH

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

diethyl 2-benzylmalonate

(S)-3-carbethoxy-3-benzylpiperidine

Downstream raw materials:

L-163,540

Refernces

• 1、 Maligres, Peter E.,Chartrain, Michel M.,Upadhyay, Veena,Cohen, Deborah,Reamer, Robert A.,Askin, David,Volante,Reider, Paul J.. "Preparation of (S)-3-carbethoxy-3-benzypiperidine and the growth hormone secretagogue L-163,540". . p. 9548 - 9551. Retrieved 2007/10/03.