(S)-1-N-Cbz-prolinamide supplier

Name
Z-PRO-NH2
EINECS 231-397-0
CAS No. 34079-31-7
Article Data36
CAS DataBase
Density 1.263 g/cm³
Solubility
Melting Point 90-95℃
Formula C₁₃H₁₆N₂O₃
Boiling Point 465.6 °C at 760 mmHg
Molecular Weight 248.282
Flash Point 235.4 °C
Transport Information
Appearance
Safety 36
Risk Codes 22-36/37/38
Molecular Structure
Hazard Symbols Xn
Synonyms 1-Pyrrolidinecarboxylicacid, 2-(aminocarbonyl)-, phenylmethyl ester, (S)-;1-Pyrrolidinecarboxylicacid, 2-carbamoyl-, benzyl ester, L- (8CI);(S)-1-Carbobenzoxypyrrolidine-2-carboxamide;(S-2-Carbamoylpyrrolidine-1-carboxylic acid benzyl ester;Benzyl(2S)-2-carbamoylpyrrolidine-1-carboxylate;Cbz-Pro-NH2;N-Benzyloxycarbonyl-L-prolinamide;
PSA 72.63000
LogP 1.91110

Synthetic route

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

: 34079-31-7
Z-Pro-NH2

Conditions

Conditions	Yield
With ammonium hydroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 24h;	100%
With ammonium hydroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 20℃;	100%
Stage #1: N-Benzyloxycarbonyl-L-proline With 4-methyl-morpholine; chloroformic acid ethyl ester In tetrahydrofuran at 0℃; for 0.25h; Stage #2: With ammonia In tetrahydrofuran; water at 0 - 20℃; for 15h;	100%

: 3304-59-4
N-benzyloxycarbonyl-L-proline p-nitrophenyl ester

: 34079-31-7
Z-Pro-NH2

Conditions

Conditions	Yield
With ammonia; triethylamine In methanol at 0℃; Reflux;	90%

: 61350-60-5, 61350-62-7, 89705-40-8, 106709-50-6
(S)-benzyloxycarbonyl-proline acid chloride

: 34079-31-7
Z-Pro-NH2

Conditions

Conditions	Yield
With ammonia In dichloromethane at 0 - 20℃; Large scale;	82%
With ammonia In tetrahydrofuran at 0 - 20℃; for 1h;

: 501-53-1
benzyl chloroformate

: 7531-52-4
L-prolinamide

: 34079-31-7
Z-Pro-NH2

Conditions

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃;	76%
With sodium hydroxide

: 14030-00-3
(2S)-2-[({(2S)-1-[(benzyloxy)carbonyl]tetrahydro-1H-pyrrol-2-yl}carbonyl)amino]propanoic acid

A: N2-(Benzyloxycarbonyl)-N1-(1'-hydroxyethyl)-L-prolinamid

B: 34079-31-7
Z-Pro-NH2

Conditions

Conditions	Yield
With acetic acid; N-ethyl-N,N-diisopropylamine anodic oxidation; Pt electrodes, i = 250 mA*cm-2, current equiv.: 13.4 F/mol;	A 50% B 12%

: N2-(Benzyloxycarbonyl)-N1-(1'-hydroxyethyl)-L-prolinamid

: 34079-31-7
Z-Pro-NH2

Conditions

Conditions	Yield
With trifluoroacetic acid In water at 30℃; for 6h; Yield given;

: 2766-18-9
N-carbobenzoxyprolylglycine

: 34079-31-7
Z-Pro-NH2

Conditions

Conditions	Yield
With methanol; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid 1.) anodic oxidation; Pt electrodes, i = 250 mA*cm-2, current equiv.: 16.5 F/mol, 2.) H2O, 25 deg C, 8 h; Yield given. Multistep reaction;

: (S)-2-Ethoxycarbonyloxycarbonyl-pyrrolidine-1-carboxylic acid benzyl ester

: 34079-31-7
Z-Pro-NH2

Conditions

Conditions	Yield
With ammonia In dichloromethane at -20℃; for 1h; Yield given;
With ammonium hydroxide In tetrahydrofuran at 0℃; for 0.75h; Yield given;
With ammonia In water for 4h;

: 501-53-1
benzyl chloroformate

D-lysine: D-lysine

: 34079-31-7
Z-Pro-NH2

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / aq. NaOH / 2 h / 5 °C 2: 96 percent / di-tert-butyl pyrocarbonate; ammonium hydrogencarbonate; pyridine / acetonitrile / 68 h View Scheme
Multi-step reaction with 2 steps 1.1: Boc2O 1.2: 96 percent / NH4HCO3 View Scheme

: 147-85-3
L-proline

: 34079-31-7
Z-Pro-NH2

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / aq. NaOH / 2 h / 5 °C 2: 96 percent / di-tert-butyl pyrocarbonate; ammonium hydrogencarbonate; pyridine / acetonitrile / 68 h View Scheme
Multi-step reaction with 2 steps 1.1: Boc2O 1.2: 96 percent / NH4HCO3 View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide / H2O / Ambient temperature 2: 1.) triethylamine, isobutyl chloroformate, 2.) ammonia / 1.) chloroform, 0 deg C, 2 h, 2.) chloroform, RT, overnight View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide / 2 h / 5 °C 2: di-tert-butyl dicarbonate; ammonium bicarbonate; pyridine / acetonitrile / 68 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: sodium hydrogencarbonate / toluene / 2 h / 10 - 20 °C 2: thionyl chloride / toluene / 4 h / Reflux 3: ammonia / dichloromethane / 0 - 20 °C / Large scale View Scheme

: 14030-00-3
(2S)-2-[({(2S)-1-[(benzyloxy)carbonyl]tetrahydro-1H-pyrrol-2-yl}carbonyl)amino]propanoic acid

: 34079-31-7
Z-Pro-NH2

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 50 percent / AcOH, EtN(i-Pr)2 / anodic oxidation; Pt electrodes, i = 250 mA*cm-2, current equiv.: 13.4 F/mol 2: 70 percent CF3COOH / H2O / 6 h / 30 °C View Scheme

: 501-53-1
benzyl chloroformate

: 34079-31-7
Z-Pro-NH2

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / H2O / Ambient temperature 2: 1.) triethylamine, isobutyl chloroformate, 2.) ammonia / 1.) chloroform, 0 deg C, 2 h, 2.) chloroform, RT, overnight View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide / 2 h / 5 °C 2: di-tert-butyl dicarbonate; ammonium bicarbonate; pyridine / acetonitrile / 68 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: sodium hydrogencarbonate / toluene / 2 h / 10 - 20 °C 2: thionyl chloride / toluene / 4 h / Reflux 3: ammonia / dichloromethane / 0 - 20 °C / Large scale View Scheme

: 124980-30-9
N-carbobenzoxy-L-proline phenylmethyl ester

: 34079-31-7
Z-Pro-NH2

Conditions

Conditions	Yield
With ammonia In methanol at 20℃; for 120h; sealed bottle;

: 60433-33-2
C16H19NO5

: 34079-31-7
Z-Pro-NH2

Conditions

Conditions	Yield
With ammonia In dichloromethane; water

: 34079-31-7
Z-Pro-NH2

: 63808-36-6
(2S)-2-cyanopyrrolidine-1-carboxylic acid benzyl ester

Conditions

Conditions	Yield
Stage #1: Z-Pro-NH2 With p-toluenesulfonyl chloride In pyridine at 100℃; for 3h; Stage #2: With hydrogenchloride In pyridine; water at 20℃;	100%
With 1,3,5-trichloro-2,4,6-triazine In N,N-dimethyl-formamide at 0 - 20℃; for 4h; Inert atmosphere;	99%
With 1,3,5-trichloro-2,4,6-triazine In N,N-dimethyl-formamide at 0 - 20℃; for 4h;	97%

: 34079-31-7
Z-Pro-NH2

: 7531-52-4
L-prolinamide

Conditions

Conditions	Yield
With 10% palladium on carbon; hydrogen In methanol for 7h;	100%
With hydrogen; palladium on activated charcoal In methanol for 9h; Ambient temperature;	88.4%
With hydrogen; palladium on activated charcoal In methanol under 2068.6 Torr; for 5h;	87%
With hydrogen; palladium In methanol for 3h;

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 34079-31-7
Z-Pro-NH2

: benzyl (2S)-2-(dimethylaminomethylenecarbamoyl)pyrrolidine-1-carboxylate

Conditions

Conditions	Yield
at 20 - 120℃; for 2h;	100%

: 34079-31-7
Z-Pro-NH2

: 63808-47-9
Cbz-L-proline thioamide

Conditions

Conditions	Yield
With Lawessons reagent In toluene at 20 - 100℃; for 3h;	100%
With Lawessons reagent In tetrahydrofuran at 65℃;	100%
With Lawessons reagent In dichloromethane at 20℃;	80%

: 31930-35-5
ethyl (E)-3-bromoacrylate

: 34079-31-7
Z-Pro-NH2

: 1005796-57-5
benzyl (S,E)-2-(3-ethoxy-3-oxoprop-1-enylcarbamoyl)pyrrolidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: Z-Pro-NH2 With cetyltrimethylammonim bromide; potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate In toluene at 50 - 55℃; for 1h; Stage #2: ethyl (E)-3-bromoacrylate In water; toluene Heating; Further stages.;	92%

: 4461-33-0
benzoyl isocyanate

: 34079-31-7
Z-Pro-NH2

: 1419208-71-1
benzyl (S)-2-((benzoylcarbamoyl)carbamoyl)pyrrolidine-1-carboxylate

Conditions

Conditions	Yield
In toluene for 2h; Inert atmosphere; Reflux;	89%

: 24424-99-5
di-tert-butyl dicarbonate

: 34079-31-7
Z-Pro-NH2

: 96308-19-9
Z-Pro-N(Boc)2

Conditions

Conditions	Yield
With dmap In acetonitrile for 5h; Ambient temperature;	87%

: 13089-11-7
methyl 3,3,3-trifluoropyruvate

: 34079-31-7
Z-Pro-NH2

: (S)-2-(2,2,2-Trifluoro-1-hydroxy-1-methoxycarbonyl-ethylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester

Conditions

Conditions	Yield
Ambient temperature;	83%

: 103-71-9
phenyl isocyanate

: 34079-31-7
Z-Pro-NH2

: 1429472-14-9
C20H21N3O4

Conditions

Conditions	Yield
In toluene for 40h; Inert atmosphere; Reflux;	82%

: 17507-56-1
ethyl 2-diazo-2-(diethoxyphosphoryl)acetate

: 34079-31-7
Z-Pro-NH2

: Ethyl 2-[(S)-2-(1-benzyloxycarbonylpyrrolidin-2-yl)carbonyl]amino-2-(diethoxyphosphoryl)acetate

Conditions

Conditions	Yield
dirhodium tetraacetate In toluene Heating;	80%
dirhodium tetraacetate In toluene for 2h; Substitution; Heating;	80%

: 24762-04-7
2-Diazo-3-oxo-butyric acid methyl ester

: 34079-31-7
Z-Pro-NH2

: 182866-68-8
(S)-2-(1-Methoxycarbonyl-2-oxo-propylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester

Conditions

Conditions	Yield
dirhodium tetraacetate In chloroform for 0.5h; Heating;	74%

: 34079-31-7
Z-Pro-NH2

: 119020-03-0, 141774-68-7
2-(S)-aminomethyl-pyrrolidine-1-carboxylic acid benzyl ester

Conditions

Conditions	Yield
Stage #1: Z-Pro-NH2 With borane In tetrahydrofuran for 7h; Heating; Stage #2: With hydrogenchloride for 6h; Heating; Further stages.;	74%
Stage #1: Z-Pro-NH2 With borane In tetrahydrofuran at 0℃; for 7h; Heating / reflux; Stage #2: With hydrogenchloride; water In tetrahydrofuran at 0℃; for 6h; Heating / reflux; Stage #3: With sodium hydroxide In tetrahydrofuran; water pH=8;	74%

: 1248344-51-5
(S)-ethyl 5-phenyl-4-phenylselenylpent-2-(E)-enoate

: 34079-31-7
Z-Pro-NH2

: (S)-benzyl 2-((S)-1-ethoxycarbonyl-4-phenylbut-2-enylcarbamoyl)pyrrolidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: (S)-ethyl 5-phenyl-4-phenylselenylpent-2-(E)-enoate; Z-Pro-NH2 With toluene-4-sulfonic acid; trimethyl orthoformate In methanol for 0.5h; Stage #2: With N-chloro-succinimide; N-ethyl-N,N-diisopropylamine In methanol at 0℃; for 0.333333h;	60%

: 600-18-0
2-Oxobutyric acid

: 34079-31-7
Z-Pro-NH2

: Nα-benzyloxycarbonyl-L-prolyl-(Z)-α,β-dehydrobutyrine

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 5h; Heating;	40%

: 101-02-0
triphenyl phosphite

: 590-86-3
isovaleraldehyde

: 34079-31-7
Z-Pro-NH2

: 82818-47-1
(S)-2-[1-(Diphenoxy-phosphoryl)-3-methyl-butylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester

Conditions

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 20℃; for 48h; Reagent/catalyst;	38%

...Expand

: 32978-38-4
4-bromo-5-ethoxyfuran-2(5H)-one

: 34079-31-7
Z-Pro-NH2

A: 865838-95-5
benzyl (2S)-2-((2R)-2-ethoxy-5-oxo-2,5-dihydrofuran-3-ylcarbamoyl)pyrrolidine-1-carboxylate

B: 865838-96-6
benzyl (2S)-2-((2S)-2-ethoxy-5-oxo-2,5-dihydrofuran-3-ylcarbamoyl)pyrrolidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: Z-Pro-NH2 With cetyltrimethylammonim bromide; potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate In toluene at 50℃; for 1h; Stage #2: In water; toluene for 0.25h; Stage #3: 4-bromo-5-ethoxyfuran-2(5H)-one In water; toluene at 50℃; for 7h; Further stages.;	A 33% B n/a

...Expand

: 101-02-0
triphenyl phosphite

: 100-52-7
benzaldehyde

: 34079-31-7
Z-Pro-NH2

: C32H31N2O6P

Conditions

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 20℃; for 48h; Reagent/catalyst;	31%

...Expand

: 101-02-0
triphenyl phosphite

: 75-07-0
acetaldehyde

: 34079-31-7
Z-Pro-NH2

: 243974-35-8
C27H29N2O6P

Conditions

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 20℃; for 48h; Reagent/catalyst;	25%

...Expand

: 34079-31-7
Z-Pro-NH2

: 6398-06-7
N-benzyloxycarbonyl-L-isoglutamine

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane

: 127-17-3
2-oxo-propionic acid

: 34079-31-7
Z-Pro-NH2

: Nα-benzyloxycarbonyl-L-prolyldehydroalaninate

Conditions

Conditions	Yield
With hydroquinone In benzene for 6.5h; Heating;

: 64-17-5
ethanol

: 34079-31-7
Z-Pro-NH2

: C15H20N2O3*BF4(1-)*H(1+)

Conditions

Conditions	Yield
With triethyloxonium fluoroborate In dichloromethane for 1h; Heating;

(S)-1-N-Cbz-prolinamide Specification

The Z-Pro-NH₂, with the CAS registry number 34079-31-7, has the systematic name of benzyl (2S)-2-carbamoylpyrrolidine-1-carboxylate. It belongs to the following categories: Proline [Pro, P]; Z-Amino Acids and Derivatives; Z-Amino acid series. And it should be stored in the sealed containers at room temperature. The molecular formula of the chemical is C₁₃H₁₆N₂O₃.

The physical properties of Z-Pro-NH₂ are as followings: (1)ACD/LogP: 0.23; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.23; (4)ACD/LogD (pH 7.4): 0.23; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 31.58; (8)ACD/KOC (pH 7.4): 31.58; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 49.85 Å²; (13)Index of Refraction: 1.581; (14)Molar Refractivity: 65.55 cm³; (15)Molar Volume: 196.5 cm³; (16)Polarizability: 25.98×10^-24cm³; (17)Surface Tension: 56.7 dyne/cm; (18)Density: 1.263 g/cm³; (19)Flash Point: 235.4 °C; (20)Enthalpy of Vaporization: 72.72 kJ/mol; (21)Boiling Point: 465.6 °C at 760 mmHg; (22)Vapour Pressure: 7.61E-09 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(N)[C@H]2N(C(=O)OCc1ccccc1)CCC2
(2)InChI: InChI=1/C13H16N2O3/c14-12(16)11-7-4-8-15(11)13(17)18-9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H2,14,16)/t11-/m0/s1
(3)InChIKey: ZCGHEBMEQXMRQL-NSHDSACASA-N

Product Name

Z-PRO-NH2

Synthetic route

(S)-1-N-Cbz-prolinamide Specification

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