MK-677

Base Information

• Chemical Name: MK-677
• CAS No.: 191487-52-2
• Molecular Formula: CH₄O₃S*C₂₇H₃₆N₄O₅S
• Molecular Weight: 624.78
• Mol file: 191487-52-2.mol

Synonyms:

Chemical Property of MK-677

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of MK-677

There total 33 articles about MK-677 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:

isonipecotic acid (498-94-2) → MK-677 (191487-52-2,214962-40-0,159752-10-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 97 percent / K₂CO₃ / H₂O / 58 h / 22 °C

2: (COCl)2 / toluene; dimethylformamide / 16 h / 18 °C

3: 94 percent / H₂, DIEA, thioanisole / Pd/C / toluene / 22 h / 20 °C / 2068.6 Torr

4: 99 percent / TFA / CH₂Cl₂ / 17 h / 35 °C

5: NaBH₄ / toluene / 0.5 h / -2 °C

6: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C

7: 93 percent / H₂ / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr

8: DCC, HOBt / H₂O; various solvent(s) / 5 h / Ambient temperature

9: MsOH / ethanol / 7.5 h / 35 - 40 °C

10: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature

11: MsOH / ethanol / 35 - 40 °C

12: ethanol; ethyl acetate / 55 °C

With sodium tetrahydroborate; oxalyl dichloride; methanesulfonic acid; methyl-phenyl-thioether; hydrogen; potassium carbonate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(97)00359-1

Reference yield:

N-(benzyloxycarbonyl)piperidine-4-carboxaldehyde (138163-08-3) → MK-677 (191487-52-2,214962-40-0,159752-10-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 99 percent / TFA / CH₂Cl₂ / 17 h / 35 °C

2: NaBH₄ / toluene / 0.5 h / -2 °C

3: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C

4: 93 percent / H₂ / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr

5: DCC, HOBt / H₂O; various solvent(s) / 5 h / Ambient temperature

6: MsOH / ethanol / 7.5 h / 35 - 40 °C

7: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature

8: MsOH / ethanol / 35 - 40 °C

9: ethanol; ethyl acetate / 55 °C

With sodium tetrahydroborate; methanesulfonic acid; hydrogen; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; toluene;

DOI:10.1016/S0040-4020(97)00359-1

Reference yield:

benzyl spiro[indoline-3,4’-piperidine]-1‘-carboxylate (167484-18-6) → MK-677 (191487-52-2,214962-40-0,159752-10-0)

Guidance literature:

Multi-step reaction with 7 steps

1: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C

2: 93 percent / H₂ / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr

3: DCC, HOBt / H₂O; various solvent(s) / 5 h / Ambient temperature

4: MsOH / ethanol / 7.5 h / 35 - 40 °C

5: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature

6: MsOH / ethanol / 35 - 40 °C

7: ethanol; ethyl acetate / 55 °C

With methanesulfonic acid; hydrogen; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; ethanol; water; ethyl acetate;

DOI:10.1016/S0040-4020(97)00359-1

upstream raw materials:

methanesulfonic acid

Ibutamoren

isonipecotic acid

N-Boc-D-serine(Bzl)-OH

Refernces

• 1、 Qi, Xian Liang,Yang, Er Qun,Zhang, Jun Tao,Wang, Tao,Cao, Xiao Ping. "A facile synthesis of the spiroindoline-based growth hormone secretagogue, MK-677". . p. 661 - 664. Retrieved 2012/07/03.
• 2、 Maligres, Peter E.,Houpis, Ioannis,Rossen, Kai,Molina, Audrey,Sager, Jess,Upadhyay, Veena,Wells, Kenneth M.,Reamer, Robert A.,Lynch, Joseph E.,Askin, David,Volante,Reider, Paul J.,Houghton, Peter. "Synthesis of the orally active spiroindoline-based Growth Hormone Secretagogue, MK-677". . p. 10983 - 10992. Retrieved 2007/10/03.