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

Base Information

• Chemical Name: 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
• CAS No.: 159634-87-4
• Molecular Formula: C₃₂H₄₄N₄O₇S
• Molecular Weight: 628.79
• DSSTox Substance ID: DTXSID401098852
• Mol file: 159634-87-4.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 11
• Exact Mass: 628.29307093
• Heavy Atom Count: 44
• Complexity: 1130

Purity/Quality:

99.3% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(C)(C)C(=O)NC(COCC1=CC=CC=C1)C(=O)N2CCC3(CC2)CN(C4=CC=CC=C34)S(=O)(=O)C
• Isomeric SMILES: CC(C)(C)OC(=O)NC(C)(C)C(=O)N[C@H](COCC1=CC=CC=C1)C(=O)N2CCC3(CC2)CN(C4=CC=CC=C34)S(=O)(=O)C

Technology Process of 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

There total 32 articles about 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 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) → 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)

Guidance literature:

Multi-step reaction with 10 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

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:

N-(benzyloxycarbonyl)piperidine-4-carboxaldehyde (138163-08-3) → 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)

Guidance literature:

Multi-step reaction with 7 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

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; toluene;

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

Reference yield:

benzyl spiro[indoline-3,4’-piperidine]-1‘-carboxylate (167484-18-6) → 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)

Guidance literature:

Multi-step reaction with 5 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

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

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

upstream raw materials:

Boc-Aib-OH

C₂₃H₂₉N₃O₄S

isonipecotic acid

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

Downstream raw materials:

MK-677

Ibutamoren

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.