N-Benzyloxycarbonyl-L-proline supplier

Name
N-Benzyloxycarbonyl-L-proline
EINECS 214-557-4
CAS No. 1148-11-4
Article Data122
CAS DataBase
Density 1.309 g/cm³
Solubility
Melting Point 76-78 °C
Formula C₁₃H₁₅NO₄
Boiling Point 432.3 °C at 760 mmHg
Molecular Weight 249.266
Flash Point 215.3 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 22-24/25-36-26
Risk Codes 62-36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xn
Synonyms 1,2-Pyrrolidinedicarboxylicacid, 1-(phenylmethyl) ester, (S)-;1,2-Pyrrolidinedicarboxylic acid, 1-benzylester, L- (8CI);(2S)-1,2-Pyrrolidinedicarboxylic acid 1-(phenylmethyl) ester;(2S)-1-(Benzyloxycarbonyl)pyrrolidine-2-carboxylic acid;(S)-1-(Benzyloxycarbonyl)pyrrolidine-2-carboxylicacid;1-(Benzyloxycarbonyl)-L-proline;1-Carbobenzoxy-L-proline;Benzyloxycarbonyl-L-proline;Carbobenzoxy-L-proline;Carbobenzoxy-S-proline;Carbobenzyloxy-L-proline;Cbz-L-Pro-OH;N-Benzyloxycarbonyl-(S)-proline;N-Carbobenzyloxy-(S)-proline;N-Cbz-L-proline;N-[(Phenylmethoxy)carbonyl]-L-proline;
PSA 66.84000
LogP 1.81010

Synthetic route

: 501-53-1
benzyl chloroformate

: 147-85-3
L-proline

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

Conditions

Conditions	Yield
With sodium hydroxide In water for 13.5h; Ambient temperature;	100%
With sodium carbonate at 0 - 20℃; for 3h;	100%
With sodium hydroxide at 0℃; for 0.166667h;	97%

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

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

Conditions

Conditions	Yield
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 50℃; for 5h; Inert atmosphere;	98%
With 1,4-diaza-bicyclo[2.2.2]octane; hydrogen; palladium on activated charcoal; ethylenediamine In methanol at 20℃; under 760 Torr; for 6h; Hydrogenolysis;	76%
With dmap; hydrogen; palladium on activated charcoal; ethylenediamine In methanol at 20℃; for 3h;	75%

: 2133-40-6
L-proline methyl ester monohydrochloride

: 501-53-1
benzyl chloroformate

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

Conditions

Conditions	Yield
With water; sodium hydroxide In toluene at 0 - 5℃; Large scale;	94%
With sodium hydroxide In water at 0 - 5℃; Industrial scale;

: 1885-14-9
phenyl chloroformate

: 147-85-3
L-proline

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

Conditions

Conditions	Yield
With hydrogenchloride In sodium hydroxide; toluene	98%
With hydrogenchloride In sodium hydroxide; toluene	98%
With hydrogenchloride In sodium hydroxide; toluene	98%
With sodium hydroxide In chloroform; water	96%

: (S)-Pyrrolidine-1,2-dicarboxylic acid 2-allyl ester 1-benzyl ester

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

Conditions

Conditions	Yield
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide; mineral oil at 25℃; for 4h; Inert atmosphere;	97%

: 6216-63-3
N-Cbz-Prolinol

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

Conditions

Conditions	Yield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; trichloroisocyanuric acid; sodium hydrogencarbonate; sodium bromide In water; acetone at 20℃; for 24h;	100%
With sodium chlorite; Me-AZADO+BF4- In acetonitrile at 25℃; for 1.5h; pH=6.7; aq. phosphate buffer;

: 72-18-4
L-valine

: 501-53-1
benzyl chloroformate

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

Conditions

Conditions	Yield
With sodium hydroxide at 0℃;	95%

: 107196-98-5
N-nosyl-L-proline

: 501-53-1
benzyl chloroformate

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

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydroxide; sodium methylate; triethylamine In methanol; water; N,N-dimethyl-formamide	45.5%

: 5211-23-4
N-carbobenzyloxy-L-proline methyl ester

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

Conditions

Conditions	Yield
With lithium hydroxide monohydrate; water In tetrahydrofuran; methanol at 20℃; for 16h;

aqueous K2 CO3: aqueous K2 CO3

: 60-29-7
diethyl ether

: 99464-81-0
benzyl (1-chloroethyl) carbonate

: 147-85-3
L-proline

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

Conditions

Conditions	Yield
In methanol; water; ethyl acetate; Petroleum ether	88%

...Expand

: (S)-Pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-(3-methyl-but-2-enyl) ester

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

Conditions

Conditions	Yield
With sodium hydrogen sulfate; silica gel In dichloromethane at 20℃; for 6h;	93%

: 96452-48-1
benzyl pyridin-2-yl carbonate

: 147-85-3
L-proline

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

Conditions

Conditions	Yield
In chloroform; water; triethylamine for 5h; Ambient temperature;	95%
With triethylamine In water; N,N-dimethyl-formamide for 0.3h; Ambient temperature;	88%

: 147-85-3
L-proline

: 250296-57-2
N-Benzyloxycarbonyl-N-trifluoromethylsulfonyl-4-trifluoromethylanilide

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

Conditions

Conditions	Yield
With water; triethylamine In 1,4-dioxane at 20℃; for 3h; Acylation;	84%

: 91285-94-8
O-benzyl S-(pyridin-2-yl)carbonothioate

: 147-85-3
L-proline

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

Conditions

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide for 1h; Ambient temperature;	85%

: dimethylsulfonium methyl sulfate

: 147-85-3
L-proline

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

Conditions

Conditions	Yield
With triethylamine In water Ambient temperature;	86%

: 31139-36-3
dibenzyl dicarbonate

: 147-85-3
L-proline

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

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane for 1h; Ambient temperature;	83%

: 75819-24-8
3-benzyloxycarbonyl-2-oxazolone

: 147-85-3
L-proline

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

Conditions

Conditions	Yield
With triethylamine In water; acetone Ambient temperature;	93%

: 57710-80-2
1-benzyloxycarbonyl-1Hbenzo[d][1.2.3]triazole

: 147-85-3
L-proline

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

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane for 24h; Ambient temperature;	84%

: 71461-30-8
(S)-2-formylpyrrolidine-1-carboxylic acid benzyl ester

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

Conditions

Conditions	Yield
With sodium chlorite; disodium hydrogenphosphate In various solvent(s) for 1h;	90.5%

: 108645-62-1
N-benzyloxycarbonylproline methyl ester

A: 182210-00-0
methyl (2R)-(benzyloxycarbonyl)pyrrolidine-2-carboxylate

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

Conditions

Conditions	Yield
With Candida antarctica lipase In phosphate buffer at 30℃; for 38h;	A 46% B 46%

: 501-53-1
benzyl chloroformate

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / Et3N / acetonitrile / 2 h / 5 °C 2: 86 percent / Et3N / H2O / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 80 percent / (C2H5)3N / CH2Cl2 / 1 h / Ambient temperature 2: 88 percent / (C2H5)3N / dimethylformamide; H2O / 0.3 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 89 percent / quinoline; CH2Cl2 / 12 h / Ambient temperature 2: 95 percent / triethylamine; CHCl3; H2O / 5 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 20 °C 2: lithium hydroxide monohydrate; water / tetrahydrofuran; methanol / 16 h / 20 °C View Scheme

: 100-51-6
benzyl alcohol

Fmoc-Pro-Wang resin: Fmoc-Pro-Wang resin

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

Conditions

Conditions	Yield
Stage #1: benzyl alcohol; Fmoc-Pro-Wang resin With tributylphosphine; triethylamine; 1,1'-azodicarbonyl-dipiperidine In 1-methyl-pyrrolidin-2-one at 20℃; for 20h; Solid phase reaction; esterification; Mitsunobu reaction; Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 0.5h; Hydrolysis;	81 % Spectr.

: 13139-17-8
N-(Benzyloxycarbonyloxy)succinimide

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / Et3N / tetrahydrofuran / 17 h / 20 °C 2: 76 percent / H2; 1,4-diazabicyclo[2.2.2]octane / Pd/C-ethylenediamine / methanol / 6 h / 20 °C / 760 Torr View Scheme

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

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / Et3N / tetrahydrofuran / 17 h / 20 °C 2: 76 percent / H2; 1,4-diazabicyclo[2.2.2]octane / Pd/C-ethylenediamine / methanol / 6 h / 20 °C / 760 Torr View Scheme

: C20H22N4O4*H(1+)

A: C7H9N3O*H(1+)

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

Conditions

Conditions	Yield
With L-Phenylalanine amide; sodium chloride; calcium chloride In N,N-dimethyl-formamide at 25℃; for 3h; pH=8; aq. buffer;	A n/a B 5%

: 75315-63-8
N-(benzyloxycarbonyl)succinimide

: 147-85-3
L-proline

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

Conditions

Conditions	Yield
With sodium hydrogencarbonate	82%

: 136963-34-3
methyl 4-bromo-5,6-O-isopropylidene-2,3,4-trideoxy-D-threo-hexonate

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

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 65 percent / LiN3 / dimethylformamide / 168 h / Ambient temperature 2: 77 percent / DIBAL / light petroleum; toluene; hexane / 1 h / -78 °C 3: 62.5 percent / H2 / 10percent Pd/C / methanol / 6 h / 760 Torr 4: 65 percent / NaHCO3 / aq. ethanol 5: 90 percent / 80percent aq. AcOH / 120 h / Ambient temperature 6: 80 percent / aq. NaIO4 / methanol / 2 h 7: 90.5 percent / aq. NaClO2, Na2HPO4 / various solvent(s) / 1 h View Scheme

Yield

Multi-step reaction with 7 steps
1: 65 percent / LiN3 / dimethylformamide / 168 h / Ambient temperature
2: 77 percent / DIBAL / light petroleum; toluene; hexane / 1 h / -78 °C
3: 62.5 percent / H2 / 10percent Pd/C / methanol / 6 h / 760 Torr
4: 65 percent / NaHCO3 / aq. ethanol
5: 90 percent / 80percent aq. AcOH / 120 h / Ambient temperature
6: 80 percent / aq. NaIO4 / methanol / 2 h
7: 90.5 percent / aq. NaClO2, Na2HPO4 / various solvent(s) / 1 h
View Scheme

: 200499-61-2
(S)-4-Azido-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyraldehyde

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

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 62.5 percent / H2 / 10percent Pd/C / methanol / 6 h / 760 Torr 2: 65 percent / NaHCO3 / aq. ethanol 3: 90 percent / 80percent aq. AcOH / 120 h / Ambient temperature 4: 80 percent / aq. NaIO4 / methanol / 2 h 5: 90.5 percent / aq. NaClO2, Na2HPO4 / various solvent(s) / 1 h View Scheme

: 200499-59-8
(S)-4-Azido-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyric acid methyl ester

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

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 77 percent / DIBAL / light petroleum; toluene; hexane / 1 h / -78 °C 2: 62.5 percent / H2 / 10percent Pd/C / methanol / 6 h / 760 Torr 3: 65 percent / NaHCO3 / aq. ethanol 4: 90 percent / 80percent aq. AcOH / 120 h / Ambient temperature 5: 80 percent / aq. NaIO4 / methanol / 2 h 6: 90.5 percent / aq. NaClO2, Na2HPO4 / various solvent(s) / 1 h View Scheme

: 501-53-1
benzyl chloroformate

: 609-36-9
rac-Pro-OH

A: 6404-31-5
Z-D-proline

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

Conditions

Conditions	Yield
With sodium hydrogencarbonate; sodium carbonate In water; acetonitrile at 50℃; for 1h; pH=9.5; Substitution;

...Expand

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

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

Conditions

Conditions	Yield
With oxalyl dichloride; N,N-dimethyl-formamide	100%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 0.5h;	100%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 0.5h;	100%

: 186581-53-3, 908094-01-9
diazomethane

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

: 5211-23-4
N-carbobenzyloxy-L-proline methyl ester

Conditions

Conditions	Yield
In diethyl ether	100%
In diethyl ether for 3h; Ambient temperature;

: 67-56-1
methanol

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

: 5211-23-4
N-carbobenzyloxy-L-proline methyl ester

Conditions

Conditions	Yield
With thionyl chloride rt., 1 h, then reflux, 2 h;	100%
With thionyl chloride In dichloromethane 1.) -10 deg C, 2 h, 2.) RT, overnight;	99%
With thionyl chloride Inert atmosphere;	96%

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

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

: 16881-39-3
(S)-2-tert-butyl-1-benzylpyrrolidine-1,2-dicarboxylate

Conditions

Conditions	Yield
With dmap In tert-butyl alcohol for 0.916667h; Ambient temperature;	100%
With dmap In neat (no solvent) for 1h; Milling;	67%
With pyridine; dmap; 1-amino-3-(dimethylamino)propane 1.) t-BuOH, EtOAc, 15 to 20 deg C, 16-20 h, 2.) t-BuOH, EtOAc, 15 min; Yield given. Multistep reaction;
With polyethylene-g-polyacrylic acid immobilized dimethylaminopyridine In toluene at 20℃; for 76h; Flow reactor;

: 2627-86-3
(S)-1-phenyl-ethylamine

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

: 167389-05-1
(2S)-2-((1S)-1-phenylethylcarbamoyl)pyrrolidine-1-carboxylic acid benzyl ester

Conditions

Conditions	Yield
With 4-methyl-morpholine; chloroformic acid ethyl ester In ethyl acetate at 0 - 20℃; for 15h; Inert atmosphere; Schlenk technique;	100%
With nickel ferrite nanoparticle In neat (no solvent) for 0.166667h; Irradiation; Sealed tube;	58%
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide Ambient temperature;
With dicyclohexyl-carbodiimide In dichloromethane at 20℃;

: 3182-95-4
L-Phenylalaninol

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

: 88084-14-4
benzyl 2-[(1-benzyl-2-hydroxyethyl)carbamoyl]pyrrolidine-1-carboxylate

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 25℃; for 2.5h;	100%
Stage #1: N-Benzyloxycarbonyl-L-proline With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran; N,N-dimethyl-formamide at -9 - -5℃; for 0.1h; Stage #2: L-Phenylalaninol In tetrahydrofuran; N,N-dimethyl-formamide at -5 - 20℃; for 20h; Solvent; Temperature; Reagent/catalyst;	95%
With 4-methyl-morpholine; chloroformic acid ethyl ester In ethyl acetate at -15 - 20℃; for 15h; Inert atmosphere; Schlenk technique;	75%
Stage #1: N-Benzyloxycarbonyl-L-proline With TEA; chloroformic acid ethyl ester In tetrahydrofuran at 0℃; for 0.5h; Stage #2: L-Phenylalaninol In tetrahydrofuran for 20h;

: 1668-10-6
glycinamide hydrochloride

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

: 35010-96-9
Nα-benzyloxycarbonyl-L-prolyl-glycinamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	100%
Stage #1: N-Benzyloxycarbonyl-L-proline With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; Stage #2: glycinamide hydrochloride With triethylamine In tetrahydrofuran at 20℃; Further stages.;	53%
With 4-methyl-morpholine; isobutyl chloroformate 1) DMF, -15 deg C, 15 min, 2) -10 deg C, 14h; Yield given. Multistep reaction;

: 623-33-6
glycine ethyl ester hydrochloride

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

: 2766-31-6
ethyl (N-benzoxycarbonyl-L-prolyl)glycinate

Conditions

Conditions	Yield
Stage #1: N-Benzyloxycarbonyl-L-proline With 1,1'-carbonyldioxydi[2(1H)-pyridone] In dichloromethane at 20℃; Stage #2: glycine ethyl ester hydrochloride With triethylamine In dichloromethane at -18℃;	100%
Stage #1: N-Benzyloxycarbonyl-L-proline With iodine; N-ethyl-N,N-diisopropylamine; phosphorous acid trimethyl ester In ethyl acetate for 0.166667h; Cooling with ice; Inert atmosphere; Stage #2: glycine ethyl ester hydrochloride In ethyl acetate at 20℃; for 6h; Inert atmosphere; Cooling with ice;	87%
With 2,6-dimethylpyridine; 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate In tetrahydrofuran; water at 20 - 25℃; Solvent;	85%
With N,N'-dicyclopentylcarbodiimide; triethylamine In dichloromethane for 24h;	62%
With Lawessons reagent; triethylamine 1.) CH2Cl2, 20 min, room temperature 2.) 0 deg C for 1 h, room temperature for 15 h.; Yield given. Multistep reaction;

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

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

: 23631-72-3
N-carbobenzoxy-L-prolyl-L-phenylalanine methyl ester

Conditions

Conditions	Yield
With N-Ethylmaleimide; benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 25℃; for 18h; pH 7.0-7.5;	100%
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 19h;	92%
With triethylamine; 2-Pyridon-1-yl diphenyl phosphate In N,N-dimethyl-formamide for 3h; Ambient temperature;	85%

: 132139-30-1
Gly-NHC6H13*HCl

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

: 150881-08-6
Z-L-Pro-Gly-NHC6H13

Conditions

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In dichloromethane for 4h;	100%

: 75-31-0
isopropylamine

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

: 80090-63-7
(S)-N-isopropyl-(Nα-benzyloxycarbonyl)prolinamide

Conditions

Conditions	Yield
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 0 - 25℃; for 2.5h;	100%
With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide	85%

: Gly-NHC4H9*HCl

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

: 150881-06-4
Z-L-Pro-Gly-NHC4H9

Conditions

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In dichloromethane for 4h;	100%

: 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%

: 64-17-5
ethanol

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

: 51207-69-3
1,2-pyrrolidinedicarboxylic acid 2-ethyl 1-(phenylmethyl) ester

Conditions

Conditions	Yield
With (+)-10-camphorsulfonic acid for 20h; Heating;	100%
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline for 5h; Heating;	88%

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

: 147-85-3
L-proline

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethyl acetate at 80℃; for 0.0833333h; Microwave irradiation;	100%
With hydrogen; hydroxyapatite-bound Pd In methanol at 40℃; for 1h;	99%
With hydrogen; palladium on activated charcoal In ethyl acetate at 80℃; under 2585.81 Torr; for 0.0833333h; microwave irradiation;	99%

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

: N-Cbz-(S)-pyrrolidine-2-carboxylic anhydride

Conditions

Conditions	Yield
With 1,3-dimethyl-chloroimidazolinium chloride; triethylamine In dichloromethane at 20℃; for 3h;	100%

: 112275-50-0
tert-butyl 1,4-diazepine-1-carboxylate

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

: 479234-51-0
4-(1-benzyloxycarbonyl-pyrrolidine-2-carbonyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane	100%

: 3196-73-4
methyl 3-aminopropanoate hydrochloride

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

: 59543-05-4
N-benzyloxycarbonyl-L-prolyl-β-alanine methyl ester

Conditions

Conditions	Yield
Stage #1: N-Benzyloxycarbonyl-L-proline With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -25℃; for 0.166667h; Stage #2: methyl 3-aminopropanoate hydrochloride With 4-methyl-morpholine In tetrahydrofuran at -25℃; for 2h;	100%

: 541-41-3
chloroformic acid ethyl ester

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

: 1-Benzyloxycarbonyl-(2S)-carbamoylpyrrolidine

Conditions

Conditions	Yield
With 4-methyl-morpholine; ammonium hydroxide In tetrahydrofuran	100%

: 104871-99-0, 104872-00-6, 104872-03-9, 104872-05-1, 104872-06-2, 104872-07-3, 104872-19-7, 68711-40-0
(3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one

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

: 1072902-89-6
N-[(phenylmethoxy)carbonyl]-L-proline-(1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester

Conditions

Conditions	Yield
With dmap; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 0 - 25℃; for 72h; Inert atmosphere;	100%
Stage #1: N-Benzyloxycarbonyl-L-proline With dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 0.25h; Stage #2: (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one With dmap In N,N-dimethyl-formamide at 20℃;	96%

: 24544-04-5
2,6-diisopropylbenzenamine

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

: C25H32N2O3

Conditions

Conditions	Yield
With 4-methyl-morpholine; chloroformic acid ethyl ester In ethyl acetate at 0 - 20℃; for 15h; Inert atmosphere; Schlenk technique;	100%
With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran

: 143005-79-2
(S)-(3-bromo-4,5-dihydroisoxazol-5-yl)methanamine

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

: (S)-benzyl 2-((((S)-3-bromo-4,5-dihydroisoxazol-5-yl)methyl)carbamoyl)pyrrolidine-1-carboxylate

Conditions

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 0.5h;	100%

: 67-51-6
3,5-dimethyl-1H-pyrazole

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

: 182967-41-5
(S)-2-(3,5-Dimethyl-pyrazole-1-carbonyl)-pyrrolidine-1-carboxylic acid benzyl ester

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane 1.) 0 deg C, 30 min, 2.) room temperature, overnight;	99.5%

: 100-01-6
4-nitro-aniline

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

: 21027-63-4
benzyl (2S)-2-[(4-nitrophenyl)carbamoyl]pyrrolidine-1-carboxylate

Conditions

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 80℃; Inert atmosphere;	99%
With pyridine; phosphorus trichloride 1.) -10 deg C, 15 min, 2.) a) 60 deg C, 3 h, b) RT, overnight; Yield given. Multistep reaction;

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

: 6216-63-3
N-Cbz-Prolinol

Conditions

Conditions	Yield
With dimethylsulfide borane complex	99%
With borane-dimethyl sulfide complex In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	99%
With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; for 25h; Inert atmosphere;	99%

: 144222-22-0
tert-butyl 4-(aminomethyl)piperidine-1-carboxylate

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

: 4-[[[[1-[(Phenylmethoxy)carbonyl]-2(S)-pyrrolidinyl]carbonyl]amino]methyl]-1-piperidinecarboxylic acid, 1,1-dimethylethyl ester

Conditions

Conditions	Yield
	99%

: 1226972-28-6
H-allo-Ile-OTMSE

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

: 1226972-32-2
C24H38N2O5Si

Conditions

Conditions	Yield
With 2,4,6-trimethyl-pyridine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In dichloromethane at 20℃; for 24h;	99%

: 496-15-1
1-indoline

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

: 608880-11-1
benzyl (S)-(-)-2-(1-indolinylcarbonyl)-1-pyrrolidinecarboxylate

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at -5 - 25℃; Inert atmosphere;	99%

N-Benzyloxycarbonyl-L-proline Specification

The IUPAC name of N-Carbobenzoxy-L-proline is 1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid . With the CAS registry number 1148-11-4, it is also named as 1-(Benzyloxycarbonyl)proline ; Benzyloxycarbonyl-L-proline ; Benzyloxycarbonylproline ; Carbobenzoxy-L-proline ; Carbobenzoxy-S-proline ; L-1,2-Pyrrolidinedicarboxylic acid 1-benzyl ester ; 1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester, (S)- (9CI) .

The N-Carbobenzoxy-L-proline is white to light yellow crystal powder which should be stored at the temperature of 2-8 °C. It is harmful by inhalation, in contact with skin and if swallowed. And it is irritating to eyes, respiratory system and skin. Risk of impaired fertility. So people should not breathe dust and avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.17 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): -0.35 ; (4)ACD/LogD (pH 7.4): -2.07 ; (5)ACD/BCF (pH 5.5): 1 ; (6)ACD/BCF (pH 7.4): 1 ; (7)ACD/KOC (pH 5.5): 3.13 ; (8)ACD/KOC (pH 7.4): 1 ; (9)#H bond acceptors: 5 ; (10)#H bond donors: 1 ; (11)#Freely Rotating Bonds: 4 ; (12)Index of Refraction: 1.582 ; (13)Molar Refractivity: 63.55 cm³ ; (14)Molar Volume: 190.3 cm³ ; (15)Polarizability: 25.19×10^-24 cm³ ; (16)Surface Tension: 58.5 dyne/cm ; (17)Enthalpy of Vaporization: 72.53 kJ/mol ; (18)Vapour Pressure: 3.06E-08 mmHg at 25°C ; (19)Rotatable Bond Count: 4 ; (20)Exact Mass: 249.100108 ; (21)MonoIsotopic Mass: 249.100108 ; (22)Topological Polar Surface Area: 66.8 ; (23)Heavy Atom Count: 18.

People can use the following data to convert to the molecule structure. SMILES: O=C(O)[C@@H]2N(C(=O)OCc1ccccc1)CCC2; InChI: InChI=1/C13H15NO4/c15-12(16)11-7-4-8-14(11)13(17)18-9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H,15,16)/t11-/m1/s1.

The following is the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intravaginal	> 1gm/kg (1000mg/kg)		Journal of Pharmaceutical Sciences. Vol. 68, Pg. 696, 1979.

Product Name

N-Benzyloxycarbonyl-L-proline

Synthetic route

N-Benzyloxycarbonyl-L-proline Specification

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