Ibutamoren

Base Information

• Chemical Name: Ibutamoren
• CAS No.: 159634-47-6
• Molecular Formula: C27H36N4O5S
• Molecular Weight: 528.673
• European Community (EC) Number: 808-810-3
• UNII: GJ0EGN38UL
• DSSTox Substance ID: DTXSID90166700
• Nikkaji Number: J672.164H
• Wikipedia: Ibutamoren
• Wikidata: Q5984942
• NCI Thesaurus Code: C97488
• RXCUI: 1805438
• Pharos Ligand ID: 2K344T2UYXHH
• ChEMBL ID: CHEMBL13817
• Mol file: 159634-47-6.mol

Synonyms:ibutamoren mesylate;L 163,191;L 163191;L-163,191;L-163191;MK 0677;MK-0677;MK-677

Chemical Property of Ibutamoren

Chemical Property:

• Refractive Index: 1.631
• PKA: 15.73±0.46(Predicted)
• PSA: 130.42000
• Density: 1.32 g/cm³
• LogP: 3.94020
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 528.24064144
• Heavy Atom Count: 37
• Complexity: 920

Purity/Quality:

99%, ^*data from raw suppliers

MK-677 HYDROCHLORIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C(=O)NC(COCC1=CC=CC=C1)C(=O)N2CCC3(CC2)CN(C4=CC=CC=C34)S(=O)(=O)C)N
• Isomeric SMILES: CC(C)(C(=O)N[C@H](COCC1=CC=CC=C1)C(=O)N2CCC3(CC2)CN(C4=CC=CC=C34)S(=O)(=O)C)N
• Recent ClinicalTrials: Growth Hormone Secretagogue MK-0677's Effect on Lean Body Mass in Chronic Kidney Disease Stage 4/5 Subjects
• Description: Ibutamoren (INN) (developmental code names MK-677, MK-0677, L-163,191)is a non-peptidic, potent, long acting, orally-active, and selective agonist of the ghrelin receptor and a growth hormone secretagogue, mimicking the growth hormone (GH)-stimulating action of the endogenous hormone ghrelin. It has been demonstrated to increase the release of, and produces sustained increases in plasma levels of several hormones including GH and insulin-like growth factor 1 (IGF-1), but without affecting cortisol levels. MK677 has shown to sustain activation of GH-IGF-1 Axis and increase in lean body mass but no change in total fat mass or visceral fat. It is currently under development as a potential treatment for reduced levels of these hormones, such as in children or elderly adults with growth hormone deficiency, and human studies have shown it to increase both muscle mass and bone mineral density, making it a promising therapy for the treatment of frailty in the elderly.
• Uses: Growth hormone releasing factor.

Technology Process of Ibutamoren

There total 15 articles about Ibutamoren 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:

N-[(R)-[(1,2-Dihydro-1-methanesulfonylspiro[3H-indole-3,4'-piperidin]-1'-yl)carbonyl]-2-(phenylmethyloxy)ethyl]-2-[(1,1-dimethyl-ethoxy)carbonyl]amino-2-methyl-propanamide (159634-87-4) → Ibutamoren (159634-47-6)

Guidance literature:

With methanesulfonic acid; In ethanol; at 35 - 40 ℃; Yield given;

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

Reference yield:

isonipecotic acid (498-94-2) → Ibutamoren (159634-47-6)

Guidance literature:

Multi-step reaction with 11 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

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; N,N-dimethyl-formamide; toluene;

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

Reference yield:

1-benzyloxycarbonylpiperidine-4-carboxylic acid (10314-98-4) → Ibutamoren (159634-47-6)

Guidance literature:

Multi-step reaction with 10 steps

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

2: 94 percent / H₂, DIEA, thioanisole / Pd/C / toluene / 22 h / 20 °C / 2068.6 Torr

3: 99 percent / TFA / CH₂Cl₂ / 17 h / 35 °C

4: NaBH₄ / toluene / 0.5 h / -2 °C

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

6: 93 percent / H₂ / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr

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

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

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

10: MsOH / ethanol / 35 - 40 °C

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

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

upstream raw materials:

N-[(R)-[(1,2-Dihydro-1-methanesulfonylspiro[3H-indole-3,4'-piperidin]-1'-yl)carbonyl]-2-(phenylmethyloxy)ethyl]-2-[(1,1-dimethyl-ethoxy)carbonyl]amino-2-methyl-propanamide

isonipecotic acid

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

benzyl bromide

Downstream raw materials:

MK-677

Refernces

• 1、 -. "Spiro piperidines and homologs which promote release of growth hormone". . . Retrieved 2008/06/13.