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117928-94-6

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Basic Information
CAS No.: 117928-94-6
Name: GLYX 13
Article Data: 3
Molecular Structure:
Molecular Structure of 117928-94-6 (GLYX 13)
Formula: C18H31N5O6
Molecular Weight: 413.474
Synonyms: GLYX 13
Density: 1.37 g/cm3
Boiling Point: 844.212 °C at 760 mmHg
Flash Point: 464.363 °C
PSA: 179.29000
LogP: -1.30530
Related products
Synthetic route

Fmoc-Thr-Pro-Pro-ThrNH2

117928-94-6

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

Conditions
ConditionsYield
With Octanethiol; tert-butylamine In N,N-dimethyl-formamide at 20℃; for 0.5h;97%

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

117928-94-6

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

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; under 2250.23 - 3000.3 Torr; Large scale;95%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 2327.23 - 3102.97 Torr; Industrial scale;43.5%

(S)-benzyl 2-((S)-2-((2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-ylcarbamoyl)pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate

117928-94-6

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2327.23 - 3102.97 Torr / Industrial scale
2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-methyl-morpholine / ethanol / -5 - 0 °C / Industrial scale
2.2: -5 - 35 °C / Industrial scale
3.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2327.23 - 3102.97 Torr / Industrial scale
View Scheme
Multi-step reaction with 4 steps
1: hydrogenchloride; hydrogen; palladium 10% on activated carbon / water; ethanol / 20 °C / 2327.23 - 3102.97 Torr
2: 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / ethanol / -5 - 20 °C
3: hydrogenchloride / dichloromethane; tetrahydrofuran; water / 0 - 5 °C
4: hydrogen; palladium 10% on activated carbon / ethanol / 20 °C / 2250.23 - 3000.3 Torr / Large scale
View Scheme

(S)-N-((2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl)-1-((S)-pyrrolidine-2-carbonyl)pyrrolidine-2-carboxamide

117928-94-6

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-methyl-morpholine / ethanol / -5 - 0 °C / Industrial scale
1.2: -5 - 35 °C / Industrial scale
2.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2327.23 - 3102.97 Torr / Industrial scale
View Scheme
Multi-step reaction with 3 steps
1: 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / ethanol / -5 - 20 °C
2: hydrogenchloride / dichloromethane; tetrahydrofuran; water / 0 - 5 °C
3: hydrogen; palladium 10% on activated carbon / ethanol / 20 °C / 2250.23 - 3000.3 Torr / Large scale
View Scheme
147-85-3

L-proline

117928-94-6

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

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: thionyl chloride / 0 - 25 °C / Industrial scale
2.1: dicyclohexyl-carbodiimide; triethylamine / dichloromethane / 0 - 30 °C / Industrial scale
3.1: lithium hydroxide; water / tetrahydrofuran / 18 h / 20 - 30 °C / Industrial scale
4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-methyl-morpholine / dichloromethane / 0.5 h / -5 - 5 °C / Industrial scale
4.2: 22 h / -5 - 30 °C / Industrial scale
5.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2327.23 - 3102.97 Torr / Industrial scale
6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-methyl-morpholine / ethanol / -5 - 0 °C / Industrial scale
6.2: -5 - 35 °C / Industrial scale
7.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2327.23 - 3102.97 Torr / Industrial scale
View Scheme
Multi-step reaction with 8 steps
1.1: thionyl chloride / 0 - 25 °C / Industrial scale
2.1: sodium hydroxide / water / 0 - 5 °C / Industrial scale
3.1: dicyclohexyl-carbodiimide; triethylamine / dichloromethane / 0 - 30 °C / Industrial scale
4.1: lithium hydroxide; water / tetrahydrofuran / 18 h / 20 - 30 °C / Industrial scale
5.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-methyl-morpholine / dichloromethane / 0.5 h / -5 - 5 °C / Industrial scale
5.2: 22 h / -5 - 30 °C / Industrial scale
6.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2327.23 - 3102.97 Torr / Industrial scale
7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-methyl-morpholine / ethanol / -5 - 0 °C / Industrial scale
7.2: -5 - 35 °C / Industrial scale
8.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2327.23 - 3102.97 Torr / Industrial scale
View Scheme
1148-11-4

N-Benzyloxycarbonyl-L-proline

117928-94-6

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

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: dicyclohexyl-carbodiimide; triethylamine / dichloromethane / 0 - 30 °C / Industrial scale
2.1: lithium hydroxide; water / tetrahydrofuran / 18 h / 20 - 30 °C / Industrial scale
3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-methyl-morpholine / dichloromethane / 0.5 h / -5 - 5 °C / Industrial scale
3.2: 22 h / -5 - 30 °C / Industrial scale
4.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2327.23 - 3102.97 Torr / Industrial scale
5.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-methyl-morpholine / ethanol / -5 - 0 °C / Industrial scale
5.2: -5 - 35 °C / Industrial scale
6.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2327.23 - 3102.97 Torr / Industrial scale
View Scheme
Multi-step reaction with 6 steps
1: 4-methyl-morpholine; isobutyl chloroformate / acetonitrile / -15 °C
2: ammonium hydroxide / methanol
3: hydrogen; palladium on activated charcoal
4: 4-methyl-morpholine; pivaloyl chloride / N,N-dimethyl-formamide / -15 - 20 °C / Inert atmosphere
5: zinc dibromide / dichloromethane / 12 h / 20 °C
6: tert-butylamine; Octanethiol / N,N-dimethyl-formamide / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine / dichloromethane / 0 - 20 °C / Large scale
1.2: -10 - 20 °C / Large scale
2.1: lithium hydroxide; water / tetrahydrofuran / 20 °C
3.1: 4-methyl-morpholine; isobutyl chloroformate / dichloromethane
3.2: 20 °C
4.1: hydrogenchloride; hydrogen; palladium 10% on activated carbon / water; ethanol / 20 °C / 2327.23 - 3102.97 Torr
5.1: 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / ethanol / -5 - 20 °C
6.1: hydrogenchloride / dichloromethane; tetrahydrofuran; water / 0 - 5 °C
7.1: hydrogen; palladium 10% on activated carbon / ethanol / 20 °C / 2250.23 - 3000.3 Torr / Large scale
View Scheme
Multi-step reaction with 7 steps
1.1: 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine / dichloromethane / 0 - 20 °C / Large scale
1.2: -10 - 20 °C / Large scale
2.1: lithium hydroxide; water / tetrahydrofuran / 20 °C
3.1: triethylamine / dichloromethane / 20 °C
3.2: 20 °C
4.1: hydrogenchloride; hydrogen; palladium 10% on activated carbon / water; ethanol / 20 °C / 2327.23 - 3102.97 Torr
5.1: 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / ethanol / -5 - 20 °C
6.1: hydrogenchloride / dichloromethane; tetrahydrofuran; water / 0 - 5 °C
7.1: hydrogen; palladium 10% on activated carbon / ethanol / 20 °C / 2250.23 - 3000.3 Torr / Large scale
View Scheme
17708-83-7

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

117928-94-6

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

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: lithium hydroxide; water / tetrahydrofuran / 18 h / 20 - 30 °C / Industrial scale
2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-methyl-morpholine / dichloromethane / 0.5 h / -5 - 5 °C / Industrial scale
2.2: 22 h / -5 - 30 °C / Industrial scale
3.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2327.23 - 3102.97 Torr / Industrial scale
4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-methyl-morpholine / ethanol / -5 - 0 °C / Industrial scale
4.2: -5 - 35 °C / Industrial scale
5.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2327.23 - 3102.97 Torr / Industrial scale
View Scheme
Multi-step reaction with 6 steps
1.1: lithium hydroxide; water / tetrahydrofuran / 20 °C
2.1: 4-methyl-morpholine; isobutyl chloroformate / dichloromethane
2.2: 20 °C
3.1: hydrogenchloride; hydrogen; palladium 10% on activated carbon / water; ethanol / 20 °C / 2327.23 - 3102.97 Torr
4.1: 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / ethanol / -5 - 20 °C
5.1: hydrogenchloride / dichloromethane; tetrahydrofuran; water / 0 - 5 °C
6.1: hydrogen; palladium 10% on activated carbon / ethanol / 20 °C / 2250.23 - 3000.3 Torr / Large scale
View Scheme
Multi-step reaction with 6 steps
1.1: lithium hydroxide; water / tetrahydrofuran / 20 °C
2.1: triethylamine / dichloromethane / 20 °C
2.2: 20 °C
3.1: hydrogenchloride; hydrogen; palladium 10% on activated carbon / water; ethanol / 20 °C / 2327.23 - 3102.97 Torr
4.1: 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / ethanol / -5 - 20 °C
5.1: hydrogenchloride / dichloromethane; tetrahydrofuran; water / 0 - 5 °C
6.1: hydrogen; palladium 10% on activated carbon / ethanol / 20 °C / 2250.23 - 3000.3 Torr / Large scale
View Scheme
7360-23-8

Cbz-Pro-Pro-OH

117928-94-6

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-methyl-morpholine / dichloromethane / 0.5 h / -5 - 5 °C / Industrial scale
1.2: 22 h / -5 - 30 °C / Industrial scale
2.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2327.23 - 3102.97 Torr / Industrial scale
3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-methyl-morpholine / ethanol / -5 - 0 °C / Industrial scale
3.2: -5 - 35 °C / Industrial scale
4.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2327.23 - 3102.97 Torr / Industrial scale
View Scheme
Multi-step reaction with 5 steps
1.1: 4-methyl-morpholine; isobutyl chloroformate / dichloromethane
1.2: 20 °C
2.1: hydrogenchloride; hydrogen; palladium 10% on activated carbon / water; ethanol / 20 °C / 2327.23 - 3102.97 Torr
3.1: 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / ethanol / -5 - 20 °C
4.1: hydrogenchloride / dichloromethane; tetrahydrofuran; water / 0 - 5 °C
5.1: hydrogen; palladium 10% on activated carbon / ethanol / 20 °C / 2250.23 - 3000.3 Torr / Large scale
View Scheme
Multi-step reaction with 5 steps
1.1: triethylamine / dichloromethane / 20 °C
1.2: 20 °C
2.1: hydrogenchloride; hydrogen; palladium 10% on activated carbon / water; ethanol / 20 °C / 2327.23 - 3102.97 Torr
3.1: 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / ethanol / -5 - 20 °C
4.1: hydrogenchloride / dichloromethane; tetrahydrofuran; water / 0 - 5 °C
5.1: hydrogen; palladium 10% on activated carbon / ethanol / 20 °C / 2250.23 - 3000.3 Torr / Large scale
View Scheme
16652-71-4

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride

117928-94-6

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

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1H-imidazole; pivaloyl chloride / tetrahydrofuran; dichloromethane / -20 - -15 °C / Inert atmosphere
2: palladium on activated charcoal; triethylsilane / ethanol / 0 - 10 °C
3: 4-methyl-morpholine; pivaloyl chloride / N,N-dimethyl-formamide / -15 - 20 °C / Inert atmosphere
4: zinc dibromide / dichloromethane / 12 h / 20 °C
5: tert-butylamine; Octanethiol / N,N-dimethyl-formamide / 0.5 h / 20 °C
View Scheme

C35H40N2O6

117928-94-6

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: palladium on activated charcoal; triethylsilane / ethanol / 0 - 10 °C
2: 4-methyl-morpholine; pivaloyl chloride / N,N-dimethyl-formamide / -15 - 20 °C / Inert atmosphere
3: zinc dibromide / dichloromethane / 12 h / 20 °C
4: tert-butylamine; Octanethiol / N,N-dimethyl-formamide / 0.5 h / 20 °C
View Scheme
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  • Casno:

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    MSDS/COA Download

    GLYX 13

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    Product name: Rapastinel CAS No.: 117928-94-6 Molecule Formula：C18H31N5O6 Molecule Weight：413.47 Purity: 98.0% Package: 1g/bag Description：White powder Manufacture Standards：Enterprise Standard TESTING ITEMS

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    117928-94-6

    GLYX 13

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    GLYX13 英文同义词L-ThreoninaMide,L-threonyl-L-prolyl-L-prolyl-;GLYX-13trifluoroacetate;L-Threonyl-L-prolyl-L-prolyl-L-threoninamidetrifluorChemicalbookoacetate;GLYX13;Thr-Pro-Pro-Thr-NH2trifluoroacetate;TPPT-amidetrifluoroacetate;Rapastinel;GIYX-13 CAS号

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    117928-94-6

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    117928-94-6

    GLYX 13

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    117928-94-6

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  • Casno:

    117928-94-6

    GLYX 13

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Specification

The GLYX 13, with the CAS registry number 117928-94-6, is also known as L-Threoninamide, L-threonyl-L-prolyl-L-prolyl-. This chemical's molecular formula is C18H31N5O6 and molecular weight is 413.47. What's more, its systematic name is (2S)-1-[(2S)-1-[(2S,3R)-2-amino-3-hydroxy-butanoyl]pyrrolidine-2-carbonyl]-N-[(1S,2R)-1-carbamoyl-2-hydroxy-propyl]pyrrolidine-2-carboxamide.

Physical properties of GLYX 13 are: (1) # of Rule of 5 Violations: 2; (2)ACD/BCF (pH 5.5): 1.00; (3)ACD/BCF (pH 7.4): 1.00; (4)ACD/KOC (pH 5.5): 1.00; (5)ACD/KOC (pH 7.4): 1.00; (6)#H bond acceptors: 11; (7)#H bond donors: 7; (8)#Freely Rotating Bonds: 10; (9)Polar Surface Area: 179.29 Å2; (10)Index of Refraction: 1.59; (11)Molar Refractivity: 101.771 cm3; (12)Molar Volume: 301.7 cm3; (13)Polarizability: 40.345×10-24cm3; (14)Surface Tension: 70.734 dyne/cm; (15)Density: 1.37 g/cm3; (16)Flash Point: 464.363 °C; (17)Enthalpy of Vaporization: 139.514 kJ/mol; (18)Boiling Point: 844.212 °C at 760 mmHg; (19)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: C[C@H]([C@@H](C(=O)N1CCC[C@H]1C(=O)N2CCC[C@H]2C(=O)N[C@@H]([C@@H](C)O)C(=O)N)N)O
(2)Std. InChI: InChI=1S/C18H31N5O6/c1-9(24)13(19)18(29)23-8-4-6-12(23)17(28)22-7-3-5-11(22)16(27)21-14(10(2)25)15(20)26/h9-14,24-25H,3-8,19H2,1-2H3,(H2,20,26)(H,21,27)/t9-,10-,11+,12+,13+,14+/m1/s1
(3)Std. InChIKey: GIBQQARAXHVEGD-BSOLPCOYSA-N