(2S)-1-[(2S)-2-azaniumyl-3-(1H-indol-3-yl)propanoyl]pyrrolidine-2-carboxylate

Base Information

• Chemical Name: (2S)-1-[(2S)-2-azaniumyl-3-(1H-indol-3-yl)propanoyl]pyrrolidine-2-carboxylate
• CAS No.: 38136-75-3
• Molecular Formula: C₁₆H₁₉N₃O₃
• Molecular Weight: 301.345
• Hs Code.: 2933990090
• Mol file: 38136-75-3.mol

Synonyms:

Chemical Property of (2S)-1-[(2S)-2-azaniumyl-3-(1H-indol-3-yl)propanoyl]pyrrolidine-2-carboxylate

Chemical Property:

• Boiling Point: 626.426 °C at 760 mmHg
• Flash Point: 332.651 °C
• PSA: 99.42000
• Density: 1.389g/cm³
• LogP: 1.75150
• Storage Temp.: -15°C
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 301.14264148
• Heavy Atom Count: 22
• Complexity: 437

Purity/Quality:

98%Min ^*data from raw suppliers

H-TRP-PRO-OH 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N(C1)C(=O)C(CC2=CNC3=CC=CC=C32)[NH3+])C(=O)[O-]
• Isomeric SMILES: C1C[C@H](N(C1)C(=O)[C@H](CC2=CNC3=CC=CC=C32)[NH3+])C(=O)[O-]

Technology Process of (2S)-1-[(2S)-2-azaniumyl-3-(1H-indol-3-yl)propanoyl]pyrrolidine-2-carboxylate

There total 5 articles about (2S)-1-[(2S)-2-azaniumyl-3-(1H-indol-3-yl)propanoyl]pyrrolidine-2-carboxylate 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:

D-tryptophan (153-94-6,27732-43-0,80206-30-0,27813-82-7) → Tryptophyl-Proline (38136-75-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / diethyl ether / 0.17 h / 30 °C

2: OH^(1-) / 1) by esters of proline; 2) hydrolysis by alkali in H₂O-alcohols

With hydroxide; In diethyl ether;

DOI:10.1016/S0040-4039(01)80754-1

Reference yield:

C31H29N3O5 (251316-94-6) → tryptophan-proline (38136-75-3)

Guidance literature:

With piperidine; In N,N-dimethyl-formamide; for 0.5h;

DOI:10.1021/bi100897u

Reference yield:

4-(3-indolylmethyl)-2-trifluoromethyl-5(4H)-oxazolone (126689-19-8) → Tryptophyl-Proline (38136-75-3)

Guidance literature:

With hydroxide; Multistep reaction; 1) by esters of proline; 2) hydrolysis by alkali in H₂O-alcohols;

DOI:10.1016/S0040-4039(01)80754-1

upstream raw materials:

4-(3-indolylmethyl)-2-trifluoromethyl-5(4H)-oxazolone

D-tryptophan

1,7-dioxo-2,5,6-trimethyl-1H,7H-pyrazolo<1,2-a>pyrazol-3-yl-methylthiomethylcarbonyl-glycyl-L-tryptophyl-L-proline

1,7-dioxo-2,5,6-trimethyl-1H,7H-pyrazolo<1,2-a>pyrazol-3-yl-methylthiomethylcarbonyl-L-phenylalanyl-l-tryptophyl-L-proline

Downstream raw materials:

1,7-dioxo-2,5,6-trimethyl-1H,7H-pyrazolo<1,2-a>pyrazol-3-yl-methylthiomethylcarbonyl-L-phenylalanyl-l-tryptophyl-L-proline

brevianamide F

Refernces

• 1、 Xiang, Dao Feng,Patskovsky, Yury,Xu, Chengfu,Fedorov, Alexander A.,Fedorov, Elena V.,Sisco, Abby A.,Sauder, J. Michael,Burley, Stephen K.,Almo, Steven C.,Raushel, Frank M.. "Functional identification and structure determination of two novel prolidases from cog1228 in the amidohydrolase superfamily". experimental part. p. 6791 - 6803. Retrieved 2011/05/05.