N-(2-Pyrazinylcarbonyl)-L-phenylalanine supplier

Name
(S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID
EINECS
CAS No. 114457-94-2
Article Data26
CAS DataBase
Density 1.323 g/cm³
Solubility
Melting Point 166-169℃
Formula C₁₄H₁₃N₃O₃
Boiling Point 573.8 °C at 760 mmHg
Molecular Weight 271.276
Flash Point 300.8 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms (S)-3-Phenyl-2-[(pyrazin-2-ylcarbonyl)amino] propanoic acid;
PSA 92.18000
LogP 1.29320

Synthetic route

: (pyrazine-2-carbonyl)-L-phenylalanine ethyl ester

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions

Conditions	Yield
With sodium hydroxide In water; acetone at 0℃; for 2h;	99%

: 63-91-2
L-phenylalanine

: 306990-94-3
(1H-benzo[d][1,2,3]triazol-1-yl)(pyrazin-2-yl)methanone

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions

Conditions	Yield
With trialkylamine In water; acetonitrile at 20℃;	98%

: 7364-51-4
N,O-bis(trimethylsilyl)phenylalanine

: 103435-88-7
pyrazinecarboxylic acid imidazolide

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions

Conditions	Yield
Stage #1: N,O-bis(trimethylsilyl)phenylalanine; pyrazinecarboxylic acid imidazolide In dichloromethane at -40 - 20℃; for 19.5h; Stage #2: With water; citric acid In dichloromethane	97%
In dichloromethane at -40 - 20℃; for 16.5h;	0.96 g

: C18H21N3O3

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 2h;	96%

: 73058-37-4
N-(2-pyrazinylcarbonyl)-L-phenylalanine methyl ester

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions

Conditions	Yield
With sodium hydroxide In acetone pH=12 - Ca. 13; Cooling with ice;	93.6%
With lithium hydroxide In tetrahydrofuran; water at 0℃; for 1h;	93%
With sodium hydroxide In 1,4-dioxane; methanol for 1h;	69%

: Phe-Wang resin

: 18414-58-9
diphenylmethylsilanecarboxylic acid

: 32111-21-0
2-iodopyrazine

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions

Conditions	Yield
Stage #1: Phe-Wang resin; diphenylmethylsilanecarboxylic acid; 2-iodopyrazine With potassium fluoride; C39H32OP2C13H12N(1-)Pd(2+)*CH3O3S(1-); triethylamine In N,N-dimethyl-formamide at 20℃; for 15h; wang polystyrene resin; Sealed tube; Inert atmosphere; Stage #2: With triethylsilane; trifluoroacetic acid In water at 20℃; for 2h; Sealed tube; Inert atmosphere;	82%

...Expand

: 19847-10-0
pyrazinoyl chloride

: 63-91-2
L-phenylalanine

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions

Conditions	Yield
Stage #1: pyrazinoyl chloride; L-phenylalanine With sodium carbonate In water; toluene at 10 - 25℃; for 3h; Stage #2: With hydrogenchloride In methanol; water at 15 - 20℃; pH=3;	36%
With sodium carbonate In water; toluene at 10 - 25℃;	36%

: 179324-69-7
velcade

A: Pyrazine-2-carboxylic acid ((S)-1-carbamoyl-2-phenyl-ethyl)-amide

B: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions

Conditions	Yield
With sodium hydroxide; oxygen In dimethyl sulfoxide at 70℃; for 250h; pH=12.0; Kinetics; Product distribution; Oxidation; hydrolysis;
With sodium hydroxide; oxygen at 70℃; for 48h; pH=12; Oxidation; hydrolysis;

: 179324-69-7
velcade

A: Pyrazine-2-carboxylic acid ((S)-1-carbamoyl-2-phenyl-ethyl)-amide

B: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

C: 289472-78-2
Pyrazine-2-carboxylic acid [(S)-1-((R)-1-hydroxy-3-methyl-butylcarbamoyl)-2-phenyl-ethyl]-amide

D: Pyrazine-2-carboxylic acid [(S)-1-((S)-1-hydroxy-3-methyl-butylcarbamoyl)-2-phenyl-ethyl]-amide

Conditions

Conditions	Yield
With dihydrogen peroxide In water at 20℃; for 1h; Kinetics; Product distribution; Further Variations:; Solvents; Oxidation; hydrolysis;

...Expand

: 179324-69-7
velcade

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions

Conditions	Yield
With hydrogenchloride; oxygen In dimethyl sulfoxide at 70℃; for 250h; pH=1.0; Kinetics; Product distribution; Oxidation; hydrolysis;
With hydrogenchloride; oxygen at 70℃; for 120h; pH=1.0; Oxidation; hydrolysis;

: 98-97-5
2-pyrazylcarboxylic acid

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: BOP; DiPEA / dimethylformamide / 0.25 h 1.2: 70 percent / dimethylformamide / 1 h 2.1: 69 percent / aq. NaOH / dioxane; methanol / 1 h View Scheme
Multi-step reaction with 2 steps 1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2: lithium hydroxide / tetrahydrofuran; water / 3 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 4-methyl-morpholine / dichloromethane; acetonitrile / 5 h / -15 - 25 °C 2.1: triethylamine; water; lithium bromide / acetonitrile / 5.17 h / 0 - 20 °C 2.2: 0 - 2 °C / pH 3 - 4 View Scheme

: 7524-50-7
methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: BOP; DiPEA / dimethylformamide / 0.25 h 1.2: 70 percent / dimethylformamide / 1 h 2.1: 69 percent / aq. NaOH / dioxane; methanol / 1 h View Scheme
Multi-step reaction with 2 steps 1.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 4-methyl-morpholine / dichloromethane; acetonitrile / 5 h / -15 - 25 °C 2.1: triethylamine; water; lithium bromide / acetonitrile / 5.17 h / 0 - 20 °C 2.2: 0 - 2 °C / pH 3 - 4 View Scheme
Multi-step reaction with 2 steps 1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / -15 - 20 °C 2: lithium hydroxide; water / tetrahydrofuran / 2 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane 2: lithium hydroxide monohydrate / methanol / 14 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / tetrahydrofuran / 0.67 h / 0 °C 1.2: 12 h 2.1: lithium hydroxide / tetrahydrofuran; water / 1 h / 0 °C View Scheme

: 98-97-5
2-pyrazylcarboxylic acid

: 16480-57-2
L-phenylalanine sodium salt

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions

Conditions	Yield
Stage #1: 2-pyrazylcarboxylic acid With chloroformic acid ethyl ester; triethylamine In acetone at -5 - 30℃; for 3.5h; Stage #2: L-phenylalanine sodium salt In water; acetone at 0 - 30℃; for 18h; Product distribution / selectivity;

: 2577-90-4
methyl (2S)-2-amino-3-phenylpropanoate

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2: lithium hydroxide / tetrahydrofuran; water / 3 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / N,N-dimethyl-formamide / 20 °C 2: lithium hydroxide / tetrahydrofuran / 2 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 20 °C 2: sodium hydroxide / methanol; water / 20 °C View Scheme

: 63-91-2
L-phenylalanine

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloromethane / 16 h / 20 °C 2: dichloromethane / 16.5 h / -40 - 20 °C View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride 2: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / dichloromethane / -15 - 10 °C 3: sodium hydroxide / water View Scheme

: 15100-75-1
L-phenylalanine tert-butyl ester hydrochloride

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide / 0.08 h / 20 °C 1.2: 18 h / 20 °C 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C View Scheme

: C17H19N3O3

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions

Conditions	Yield
Stage #1: C17H19N3O3 With sodium hydroxide In water Stage #2: With hydrogenchloride In water

: 18934-70-8
2-amino-3-phenyl-propionic acid isopropyl ester

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / dichloromethane / -15 - 10 °C 2: sodium hydroxide / water View Scheme

: 7524-50-7
methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

: 1194235-01-2
(S)-methyl 3-phenyl-2-((S)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)-propanoate

Conditions

Conditions	Yield
With 4-methyl-morpholine; hydrogenchloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 2h; pH=12 - Ca. 13;	95.6%
Stage #1: (S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 0.666667h; Stage #2: methyl (2S)-2-amino-3-phenylpropanoate hydrochloride With 4-methyl-morpholine In tetrahydrofuran for 12h;	81%
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃;

: (aR,3aS,4S,6S,7aR)-hexahydro-3a,8,8-trimethyl-α-(2-methylpropyl)-4,6-methano-1,3,2-benzodioxaborole-2-methanamine 2,2,2-trifluoroacetate

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

: (1S,2S,3R,5S)-pinanediol N-(2-pyrazinecarbonyl)-L-phenylalanine-L-leucine boronate

Conditions

Conditions	Yield
Stage #1: (aR,3aS,4S,6S,7aR)-hexahydro-3a,8,8-trimethyl-α-(2-methylpropyl)-4,6-methano-1,3,2-benzodioxaborole-2-methanamine 2,2,2-trifluoroacetate With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In DMF (N,N-dimethyl-formamide) at -5 - 0℃; for 1h; Stage #2: (S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid With 4-methyl-morpholine In DMF (N,N-dimethyl-formamide) at 0℃; pH=7;	95.5%

Yield

Stage #1: (aR,3aS,4S,6S,7aR)-hexahydro-3a,8,8-trimethyl-α-(2-methylpropyl)-4,6-methano-1,3,2-benzodioxaborole-2-methanamine 2,2,2-trifluoroacetate With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In DMF (N,N-dimethyl-formamide) at -5 - 0℃; for 1h;
Stage #2: (S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid With 4-methyl-morpholine In DMF (N,N-dimethyl-formamide) at 0℃; pH=7;

95.5%

: (R)-1-amino-3-methylbutane-1-boronic acid-1-(neopentyl glycol) ester hydrochloride

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

: C24H33BN4O4

Conditions

Conditions	Yield
With 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; tert-butyl methyl ether at 0 - 20℃; for 12h; Reagent/catalyst; Solvent; Temperature; Large scale;	93%

: (R)-1-amino-3-methylbutane-1-boronic acid-1-(2-methyl-2,4-pentanediol) ester hydrochloride

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

: C25H35BN4O4

Conditions

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 24h; Large scale;	93%

: (R)-1-amino-3-methylbutane-1-boronic acid-1-(2,4-dimethyl-2,4-pentanediol) hydrochloride

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

: C26H37BN4O4

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In hexane; dichloromethane at 0 - 20℃; for 12h; Large scale;	93%

: 107-85-7
1-amino-3-methylbutane

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

: (S)-N-(1-(isopentylamino)-1-oxo-3-phenylpropan-2-yl)pyrazine-2-carboxamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere;	91%
With 6,6'-diselanediylbis(N-(2-(dimethylamino)ethyl)-N-methyl-3-nitrobenzamide); triethyl phosphite In acetonitrile at 50℃; for 16h; Molecular sieve;	78%

: 95-14-7
1,2,3-Benzotriazole

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

: (S)-N-(1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-3-phenylpropan-2-yl)pyrazine-2-carboxamide

Conditions

Conditions	Yield
Stage #1: 1,2,3-Benzotriazole With thionyl chloride In dichloromethane for 0.5h; Stage #2: (S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid In dichloromethane at -15℃;	90%

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

: Pyrazine-2-carboxylic acid ((S)-1-carbamoyl-2-phenyl-ethyl)-amide

Conditions

Conditions	Yield
Stage #1: (S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: With ammonium chloride In N,N-dimethyl-formamide at 20℃; for 12h; Reagent/catalyst; Solvent;	88.3%

: (R)-3-methyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butan-1-amine hydrochloride

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

: 1029701-48-1
bortezomib pinacol ester

Conditions

Conditions	Yield
With 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate; triethylamine In dichloromethane; ethyl acetate at 0 - 20℃; for 12h; Large scale;	88%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at -10 - -5℃; for 3h;	77%
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 5℃; for 2.5h; Large scale;

: (aR,3aS,4S,6S,7aR)-hexahydro-3a,8,8-trimethyl-α-(2-methylpropyl)-4,6-methano-1,3,2-benzodioxaborole-2-methanamine 2,2,2-trifluoroacetate

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

: 205393-22-2
N-[(1S)-1[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-2-benzyl]2-pyrazine carboxamide

Conditions

Conditions	Yield
With 4-methyl-morpholine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In dichloromethane; acetonitrile at -15 - 25℃; for 1.5h;	86%
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at -10 - 20℃; optical yield given as %de;	84%
Stage #1: (S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In dichloromethane at 25 - 30℃; for 0.166667 - 0.333333h; Stage #2: (aR,3aS,4S,6S,7aR)-hexahydro-3a,8,8-trimethyl-α-(2-methylpropyl)-4,6-methano-1,3,2-benzodioxaborole-2-methanamine 2,2,2-trifluoroacetate With N-ethyl-N,N-diisopropylamine In dichloromethane at 25 - 30℃; for 2 - 3h; Product distribution / selectivity;
Stage #1: (S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -5 - 0℃; for 0.25h; Stage #2: (aR,3aS,4S,6S,7aR)-hexahydro-3a,8,8-trimethyl-α-(2-methylpropyl)-4,6-methano-1,3,2-benzodioxaborole-2-methanamine 2,2,2-trifluoroacetate With N-ethyl-N,N-diisopropylamine In dichloromethane at 5 - 30℃; for 1h; Product distribution / selectivity;

: C11H24BNO2*C2HF3O2

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

: 1029701-48-1
bortezomib pinacol ester

Conditions

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane; toluene at 0 - 80℃; for 8h; Large scale;	86%

: 63024-26-0
methyl (S)-2-amino-3-(naphthalen-2-yl)propanoate hydrochloride

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

: 1194235-07-8
(S)-methyl 3-(naphthalen-2-yl)-2-((S)-3-phenyl-2-(pyrazine-2-carboxamido)-propanamido) propanoate

Conditions

Conditions	Yield
Stage #1: (S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 0.666667h; Stage #2: methyl (S)-2-amino-3-(naphthalen-2-yl)propanoate hydrochloride With 4-methyl-morpholine In tetrahydrofuran for 12h;	83%
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃;

: C20H30BNO2*ClH

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

: C34H41BN4O4

Conditions

Conditions	Yield
Stage #1: (S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid With benzotriazol-1-ol In dichloromethane for 0.166667h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 0.25h; Stage #3: C20H30BNO2*ClH With N-ethyl-N,N-diisopropylamine In dichloromethane	79.3%

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

: (1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxabor-ol-2-yl]butan-1-amine hydrochloride

: 205393-22-2
N-[(1S)-1[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-2-benzyl]2-pyrazine carboxamide

Conditions

Conditions	Yield
Stage #1: (S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid With benzotriazol-1-ol In dichloromethane at -5℃; for 0.333333h; Stage #2: (1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxabor-ol-2-yl]butan-1-amine hydrochloride With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at -15 - 20℃; for 3h;	79%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at -10 - -5℃; for 3h;	72%

Yield

Stage #1: (S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid With benzotriazol-1-ol In dichloromethane at -5℃; for 0.333333h;
Stage #2: (1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxabor-ol-2-yl]butan-1-amine hydrochloride With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at -15 - 20℃; for 3h;

79%

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at -10 - -5℃; for 3h;

72%

: 7732-18-5
water

: 6046-93-1
copper(II) acetate monohydrate

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

: [Cu((S)-3-phenyl-2-(pyrazine-2-carboxamido) propanoic acid-2H)(H2O)]*H2O

Conditions

Conditions	Yield
In sodium hydroxide; acetonitrile aq. NaOH; High Pressure; mixt. of Cu(OAc)2*H2O, aq. NaOH, ligand, CH3CN and water sealed in Teflon-lined autoclave and heated at 120°C for 4 d and then autoclave slowly cooled; crystals filtered off, washed with water and dried in air; elem. anal.;	78%

...Expand

: C18H26BNO2*ClH

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

: C32H37BN4O4

Conditions

Conditions	Yield
Stage #1: (S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid With benzotriazol-1-ol In dichloromethane for 0.166667h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 0.25h; Stage #3: C18H26BNO2*ClH With N-ethyl-N,N-diisopropylamine In dichloromethane	77.9%

: C15H28BNO2*C2HF3O2

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

: 1621908-72-2
N-[(1S)-1-[[[(1R)-1-[(3aS,4R,6R,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]-amino]carbonyl]-2-phenyl]-2-pyrazincarboxamide

Conditions

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 16h;	73%

: (1S,2S,3R,5S)-pinanediol L-proline boronate hydrochloride

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

: N-((S)-1-oxo-3-phenyl-1-((R)-2-((3aS,4S,6S,7aR)-3a,5,5,7a-tetramethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)pyrrolidin-1-yl)propan-2-yl)pyrazine-2-carboxamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h;	71%

: C16H30BNO2*ClH

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

: C30H41BN4O4

Conditions

Conditions	Yield
Stage #1: (S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid With benzotriazol-1-ol In dichloromethane for 0.166667h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 0.25h; Stage #3: C16H30BNO2*ClH With N-ethyl-N,N-diisopropylamine In dichloromethane	70.6%

: 6-aminobenzo[c][1,2]oxaborol-1(3H)-ol

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

: (S)-N-{1-[(1-hydroxy-1,3-dihydro-2,1-benzoxaborol-6-yl)amino]-1-oxo-3-phenylpropan-2-yl}pyrazine-2-carboxamide

Conditions

Conditions	Yield
With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 0.166667h;	53%

: 2748-02-9
L-leucine tert-butyl ester hydrochloride

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

: C24H32N4O4

Conditions

Conditions	Yield
Stage #1: L-leucine tert-butyl ester hydrochloride; (S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride at 20℃; for 3h;	38%

: leucine vinyl sulfone trifluoroacetate

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

: C22H28N4O4S

Conditions

Conditions	Yield
Stage #1: (S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane Stage #2: leucine vinyl sulfone trifluoroacetate In dichloromethane for 4h; Further stages.;	19%

N-(2-Pyrazinylcarbonyl)-L-phenylalanine Specification

The L-Phenylalanine,N-(2-pyrazinylcarbonyl)-, with the CAS registry number of 114457-94-2, is also known as (S)-3-Phenyl-2-[(pyrazin-2-ylcarbonyl)amino] propanoic acid. Its molecular formula is C₁₄H₁₃N₃O₃ and molecular weight is 271.27132. What's more, its systematic name is (2S)-3-Phenyl-2-(pyrazine-2-carbonylamino)propanoic acid.

Physical properties about the L-Phenylalanine,N-(2-pyrazinylcarbonyl)- are: (1)ACD/LogP: 0.48; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 6; (4)#H bond donors: 2; (5)#Freely Rotating Bonds: 5; (6)Polar Surface Area: 92.18 Å²; (7)Index of Refraction: 1.612; (8)Molar Refractivity: 71.33 cm³; (9)Molar Volume: 204.9 cm³; (10)Surface Tension: 63.9 dyne/cm; (11)Density: 1.323 g/cm³; (12)Flash Point: 300.8 °C; (13)Enthalpy of Vaporization: 90.45 kJ/mol; (14)Boiling Point: 573.8 °C at 760 mmHg; (15)Vapour Pressure: 5.27E-14 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(N[C@@H](Cc1ccccc1)C(O)=O)c2cnccn2
(2) InChI: InChI=1/C14H13N3O3/c18-13(12-9-15-6-7-16-12)17-11(14(19)20)8-10-4-2-1-3-5-10/h1-7,9,11H,8H2,(H,17,18)(H,19,20)/t11-/m0/s1
(3) InChIKey: DWYZPDHMMZGQAP-NSHDSACABA

Product Name

(S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID

Synthetic route

N-(2-Pyrazinylcarbonyl)-L-phenylalanine Specification

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