GLYX 13

Base Information

• Chemical Name: GLYX 13
• CAS No.: 117928-94-6
• Molecular Formula: C18H31N5O6
• Molecular Weight: 413.474
• Mol file: 117928-94-6.mol

Synonyms:GLYX 13

Chemical Property of GLYX 13

Chemical Property:

• Boiling Point: 844.212 °C at 760 mmHg
• PKA: 12.26±0.45(Predicted)
• Flash Point: 464.363 °C
• PSA: 179.29000
• Density: 1.37 g/cm³
• LogP: -1.30530
• Storage Temp.: ?20°C

Purity/Quality:

98% ^*data from raw suppliers

GLYX 13 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Rapastinel is a novel antidepressant drug approved as an adjunctive therapy for the treatment of treatment-resistant major depressive disorder. It is a centrally active, intravenously administered (non-orally active) amidated tetrapeptide (Thr-Pro-Pro-Thr-NH2) that acts as a selective, weak partial agonist (mixed antagonist/agonist) of an allosteric site at the glycine site of the NMDA receptor complex (Emax ≈ 25%).The drug is a rapid-acting and long-lasting antidepressant as well as robust cognitive enhancer by virtue of its ability to both inhibit and enhance NMDA receptor-mediated signal transduction. GLYX-13 is a long lasting and rapid acting antidepressant. Investigational drug for the treatment of depressive disoder. GLYX-13 trifluoroacetate has been used as an activator of NMDA (N-methyl-D-aspartate) receptor.

Technology Process of GLYX 13

There total 19 articles about GLYX 13 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: 97.0%

Fmoc-Thr-Pro-Pro-ThrNH2 → benzyl (S)-N-((2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl)-1-((S)-1-((2S,3R)-2-amino-3-hydroxybutanoyl)pyrrolidine-2 carbonyl)pyrrolidine-2-carboxamide (117928-94-6)

Guidance literature:

With Octanethiol; tert-butylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

DOI:10.3390/molecules23050996

Reference yield: 95.0%

benzyl (2S,3R)-1-((S)-2-((S)-2-((2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-ylcarbamoyl)pyrrolidine-1-carbonyl)pyrrolidin-1-yl)-3-hydroxy-1-oxobutan-2-ylcarbamate → benzyl (S)-N-((2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl)-1-((S)-1-((2S,3R)-2-amino-3-hydroxybutanoyl)pyrrolidine-2 carbonyl)pyrrolidine-2-carboxamide (117928-94-6)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃; under 2250.23 - 3000.3 Torr; Large scale;

Reference yield: 77.0%

Fmoc-Pro-OH (71989-31-6) + Fmoc-Thr(tBu)-OH (71989-35-0,138797-71-4) → benzyl (S)-N-((2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl)-1-((S)-1-((2S,3R)-2-amino-3-hydroxybutanoyl)pyrrolidine-2 carbonyl)pyrrolidine-2-carboxamide (117928-94-6)

Guidance literature:

Fmoc-Thr(tBu)-OH; With piperidine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 80 ℃; for 0.0833333h; Rink amide resin

With piperidine; In N,N-dimethyl-formamide; at 80 ℃; for 0.0333333h; Rink amide resin

Fmoc-Pro-OH; Fmoc-Thr(tBu)-OH; Further stages;

DOI:10.1021/acs.joc.1c01906

upstream raw materials:

L-proline

N-Benzyloxycarbonyl-L-proline

(S)-benzyl 2-((S)-2-(methoxycarbonyl)pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate

Cbz-Pro-Pro-OH

Refernces

• 1、 Bisht, Babita,Madhavan, Nandita. "Quick Access to High-Purity Peptide Drugs Bradykinin, Leuprolide Analogue, 2(PZ-128), and Rapastinel with Minimal Reagents". . p. 17667 - 17672. Retrieved 2021/12/09.
• 2、 -. "PROCESSES FOR SYNTHESIS OF DIPYRROLIDINE PEPTIDE COMPOUNDS". . . Retrieved 2017/12/27.