Product Name

  • Name

    GLYX 13

  • EINECS
  • CAS No. 117928-94-6
  • Article Data3
  • CAS DataBase
  • Density 1.37 g/cm3
  • Solubility
  • Melting Point
  • Formula C18H31N5O6
  • Boiling Point 844.212 °C at 760 mmHg
  • Molecular Weight 413.474
  • Flash Point 464.363 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 117928-94-6 (GLYX 13)
  • Hazard Symbols
  • Synonyms GLYX 13
  • PSA 179.29000
  • LogP -1.30530

Synthetic route

Fmoc-Thr-Pro-Pro-ThrNH2

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

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

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

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

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

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

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

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

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

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
L-proline
147-85-3

L-proline

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

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
N-Benzyloxycarbonyl-L-proline
1148-11-4

N-Benzyloxycarbonyl-L-proline

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

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
(S)-benzyl 2-((S)-2-(methoxycarbonyl)pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate
17708-83-7

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

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

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
Cbz-Pro-Pro-OH
7360-23-8

Cbz-Pro-Pro-OH

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

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
benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride
16652-71-4

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride

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

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

C35H40N2O6

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

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
(S)-benzyl 2-(((2S,3R)-3-hydroxy-1-methoxy-1-oxobutan-2-yl)carbamoyl)pyrrolidine-1-carboxylate

(S)-benzyl 2-(((2S,3R)-3-hydroxy-1-methoxy-1-oxobutan-2-yl)carbamoyl)pyrrolidine-1-carboxylate

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

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: ammonium hydroxide / methanol
2: hydrogen; palladium on activated charcoal
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
benzyl (S)-2-(((2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl)carbamoyl)pyrrolidine-1-carboxylate

benzyl (S)-2-(((2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl)carbamoyl)pyrrolidine-1-carboxylate

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

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: hydrogen; palladium on activated charcoal
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
Fmoc-Pro-ThrNH2

Fmoc-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

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: tert-butylamine; Octanethiol / 0.5 h / 20 °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
C29H36N2O6

C29H36N2O6

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

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: sodium hydroxide / water; N,N-dimethyl-formamide
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
(S)-N-((2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl)pyrrolidine-2-carboxamide

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

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

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: 4-methyl-morpholine; pivaloyl chloride / N,N-dimethyl-formamide / -15 - 20 °C / Inert atmosphere
2: zinc dibromide / dichloromethane / 12 h / 20 °C
3: tert-butylamine; Octanethiol / N,N-dimethyl-formamide / 0.5 h / 20 °C
View Scheme
Fmoc-Thr(tBu)-Pro-OH

Fmoc-Thr(tBu)-Pro-OH

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

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: 4-methyl-morpholine; pivaloyl chloride / N,N-dimethyl-formamide / -15 - 20 °C / Inert atmosphere
2: zinc dibromide / dichloromethane / 12 h / 20 °C
3: tert-butylamine; Octanethiol / N,N-dimethyl-formamide / 0.5 h / 20 °C
View Scheme
C37H49N5O8

C37H49N5O8

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

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: zinc dibromide / dichloromethane / 12 h / 20 °C
2: tert-butylamine; Octanethiol / N,N-dimethyl-formamide / 0.5 h / 20 °C
View Scheme
benzyl (2S,3R)-1-((S)-2-((S)-2-((2S,3R)-1-amino-3-tertiary-butyldimethylsilyloxy-1-oxobutan-2-ylcarbamoyl)pyrrolidine-1-carbonyl)pyrrolidin-1-yl)-3-hydroxy-1-oxobutan-2-ylcarbamate

benzyl (2S,3R)-1-((S)-2-((S)-2-((2S,3R)-1-amino-3-tertiary-butyldimethylsilyloxy-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

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: hydrogenchloride / dichloromethane; tetrahydrofuran; water / 0 - 5 °C
2: hydrogen; palladium 10% on activated carbon / ethanol / 20 °C / 2250.23 - 3000.3 Torr / Large scale
View Scheme
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

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

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

C23H39N5O8

C23H39N5O8

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane at 20℃; for 16h;90%
2-Hydroxybenzophenone
117-99-7

2-Hydroxybenzophenone

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

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

C31H39N5O7

C31H39N5O7

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 48h;32%
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

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

C33H51N5O10

C33H51N5O10

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / 1,4-dioxane / 16 h / 20 °C
2: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / tetrahydrofuran / 20 °C
View Scheme
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

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

C31H47N5O10

C31H47N5O10

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / 1,4-dioxane / 16 h / 20 °C
2: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / tetrahydrofuran / 20 °C
3: Grubbs catalyst first generation / dichloromethane / 72 h / 20 °C
View Scheme
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

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

C31H49N5O10

C31H49N5O10

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: triethylamine / 1,4-dioxane / 16 h / 20 °C
2: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / tetrahydrofuran / 20 °C
3: Grubbs catalyst first generation / dichloromethane / 72 h / 20 °C
4: palladium 10% on activated carbon; hydrogen / methanol / 18 h / 20 °C
View Scheme
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

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

C26H41N5O8

C26H41N5O8

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: triethylamine / 1,4-dioxane / 16 h / 20 °C
2: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / tetrahydrofuran / 20 °C
3: Grubbs catalyst first generation / dichloromethane / 72 h / 20 °C
4: palladium 10% on activated carbon; hydrogen / methanol / 18 h / 20 °C
5: hydrogenchloride / methanol; dichloromethane / 2 h / 0 - 20 °C
View Scheme
1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

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

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

C34H61N5O7

C34H61N5O7

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; for 12h;20 mg
L-Tartaric acid
87-69-4

L-Tartaric acid

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

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

rapastinel L-tartrate

rapastinel L-tartrate

Conditions
ConditionsYield
In methanol at 20℃; for 0.75h;
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

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

rapastinel hydrochloride

rapastinel hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In methanol at 20℃;
acetic acid
64-19-7

acetic acid

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

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

rapastinel acetate

rapastinel acetate

Conditions
ConditionsYield
at 20℃; for 0.5h;
succinic acid
110-15-6

succinic acid

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

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

rapastinel succinate

rapastinel succinate

Conditions
ConditionsYield
In methanol at 20℃; for 0.75h;

GLYX 13 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

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