(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate supplier

Name
N-CARBOBENZYLOXY-L-ASPARTIC ANHYDRIDE
EINECS 224-838-3
CAS No. 4515-23-5
Article Data24
CAS DataBase
Density 1.37 g/cm³
Solubility
Melting Point 123-124 °C(lit.)
Formula C₁₂H₁₁NO₅
Boiling Point 490.2 °C at 760 mmHg
Molecular Weight 249.223
Flash Point 250.3 °C
Transport Information
Appearance White Powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Asparticanhydride, N-carboxy-, N-benzyl ester, L- (8CI);Carbamic acid, (tetrahydro-2,5-dioxo-3-furanyl)-,phenylmethyl ester, (S)-;N-(Benzyloxycarbonyl)-L-aspartic acid anhydride;N-(Benzyloxycarbonyl)-L-aspartic anhydride;N-(Benzyloxycarbonyl)asparticanhydride;N-Carbobenzoxy-L-aspartic acid anhydride;N-Carbobenzoxy-L-asparticanhydride;
PSA 81.70000
LogP 1.14580

Synthetic route

: 1152-61-0
N-Cbz-L-Asp

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

Conditions

Conditions	Yield
	100%
With dicyclohexyl-carbodiimide In ethyl acetate 1.) 1 h, 0 deg C, 2.) 24 h, r.t.;	98%
With acetic anhydride for 0.0166667h; microwave irradiation;	98%

: 1152-61-0
N-Cbz-L-Asp

A: 75443-62-8
benzyl N-[(3R)-2,5-dioxotetrahydrofuran-3-yl]carbamate

B: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

Conditions

Conditions	Yield
With acetic anhydride at 20 - 45℃; for 2.25h; Product distribution; Further Variations:; Reagents; Solvents; Temperatures;

: 501-53-1
benzyl chloroformate

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 89 percent 2: 98 percent / dicyclohexylcarbodiimide / ethyl acetate / 1.) 1 h, 0 deg C, 2.) 24 h, r.t. View Scheme
Multi-step reaction with 2 steps 1: K2CO3 / H2O / Ambient temperature 2: Ac2O / acetic acid / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: K2CO3 / H2O 2: Ac2O / acetic acid View Scheme

: 100-51-6
benzyl alcohol

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene / anfangs unter Kuehlung 2: MgO; water; diethyl ether 3: acetic acid anhydride View Scheme

: 124-22-1
n-Dodecylamine

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: N-dodecyl-2-carbobenzyloxyaminosuccinamic acid

Conditions

Conditions	Yield
With triethylamine In dichloromethane for 12h;	97%
With triethylamine In dichloromethane for 12h;	97%

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: 87219-29-2
benzyl (3S)-5-oxotetrahydro-3-furanylcarbamate

Conditions

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran	91%
With sodium tetrahydroborate at 0℃; for 3h;	91%
With sodium tetrahydroborate	86%

: 62-53-3
aniline

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: 685139-81-5
benzyloxycarbonyl-L-aspartic acid dianilide

Conditions

Conditions	Yield
Stage #1: N-benzyloxycarbonyl-L-aspartic acid anhydride In dimethyl sulfoxide at 20℃; for 3h; Stage #2: aniline With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃; for 24h;	87%
Stage #1: N-benzyloxycarbonyl-L-aspartic acid anhydride In N,N-dimethyl-formamide at 20℃; for 3h; Stage #2: aniline With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃; for 24h;	87%

: 17467-35-5
3-methyl-1,2,4-thiadiazol-5-amine

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: 403736-43-6
2-benzyloxycarbonylamino-N-(3-methyl-[1,2,4]thiadiazol-5-yl)-succinamic acid

Conditions

Conditions	Yield
In dimethyl sulfoxide at 20℃; for 2h;	85%

: 100-51-6
benzyl alcohol

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: 4779-31-1
Z-Asp-OBn

Conditions

Conditions	Yield
at 90℃; for 3.5h;	82%
at 90℃; for 3.5h;	72%

: 64-17-5
ethanol

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: 4668-43-3
(S)-3-(benzyloxycarbonylamino)-4-ethoxy-4-oxobutanoic acid

Conditions

Conditions	Yield
at 20℃; for 36h;	81%
Heating;
With N-cyclohexyl-cyclohexanamine In diethyl ether
for 18h; Product distribution / selectivity; Heating / reflux;

: 6315-89-5
3,4-dimethoxyaniline

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: 932743-84-5
[1,2-bis-(3,4-dimethoxy-phenylcarbamoyl)-ethyl]-carbamic acid benzyl ester

Conditions

Conditions	Yield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃; for 24h;	79%

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: (3S)-benzyl N-(1-hydroxy-2,5-dioxo-pyrrolidin-3-yl)carbamate

Conditions

Conditions	Yield
Stage #1: N-benzyloxycarbonyl-L-aspartic acid anhydride With sodium hydroxide; hydroxylamine hydrochloride In 1,4-dioxane; water at 19.85 - 49.85℃; for 1.25h; Stage #2: at 124.85℃; for 0.333333h;	77%
With sodium hydroxide; hydroxylamine hydrochloride In 1,4-dioxane; water at 60℃; for 2h;	75%
With hydroxylamine hydrochloride; sodium carbonate In water at 0℃; for 1h;	54%

: 100-46-9
benzylamine

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: 124166-11-6
(S)-(1-benzyl-2,5-dioxo-pyrrolidin-3-yl)carbamic acid benzyl ester

Conditions

Conditions	Yield
toluene-4-sulfonic acid In DMF (N,N-dimethyl-formamide); toluene at 22 - 110℃; for 31h; Heating / reflux; Azeotropic dehydratation;	77%
toluene-4-sulfonic acid In DMF (N,N-dimethyl-formamide); toluene at 30 - 110℃; for 25h; Heating / reflux;	n/a
In ethanol at 20℃; for 18h;	n/a

: 769-92-6
4-tert-Butylaniline

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: 918309-76-9
[1,2-bis-(4-tert-butyl-phenylcarbamoyl)-ethyl]-carbamic acid benzyl ester

Conditions

Conditions	Yield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃; for 25h;	73%

: 2687-43-6
O-benzylhydoxylamine hydrochloride

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: ((S)-1-Benzyloxy-2,5-dioxo-pyrrolidin-3-yl)-carbamic acid benzyl ester

Conditions

Conditions	Yield
In toluene for 1h; Heating;	72%

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: 4668-44-4
N-benzyloxycarbonyl-L-aspartic acid α-p-nitrobenzyl ester

Conditions

Conditions	Yield
	69%

: 106-49-0
p-toluidine

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

A: (S)-3-Benzyloxycarbonylamino-N-p-tolyl-succinamic acid

B: (S)-2-Benzyloxycarbonylamino-N-p-tolyl-succinamic acid

Conditions

Conditions	Yield
With acetic acid In benzene for 0.166667h; Heating; Yields of byproduct given;	A 67% B n/a
In dimethyl sulfoxide for 0.333333h; Ambient temperature; Yield given. Yields of byproduct given;

...Expand

: 104-94-9
4-methoxy-aniline

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: [(S)-1,2-Bis-(4-methoxy-phenylcarbamoyl)-ethyl]-carbamic acid benzyl ester

Conditions

Conditions	Yield
Stage #1: N-benzyloxycarbonyl-L-aspartic acid anhydride In N,N-dimethyl-formamide at 20℃; for 3h; Stage #2: 4-methoxy-aniline With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃; for 24h;	60%

: 67-56-1
methanol

: 36282-40-3
(3-methoxyphenyl)magnesium bromide

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

A: (3S)-methyl 3-(benzyloxycarbonylamino)-4-(3-methoxyphenyl)-4-oxobutanoate

B: 35909-93-4
dimethyl (2S)-2-[(phenylmethoxy)carbonylamino]-butane-1,4-dioate

Conditions

Conditions	Yield
Stage #1: (3-methoxyphenyl)magnesium bromide; N-benzyloxycarbonyl-L-aspartic acid anhydride In tetrahydrofuran at -78℃; for 4h; Stage #2: With citric acid In tetrahydrofuran at -78 - 20℃; Stage #3: methanol With thionyl chloride	A 60% B n/a

...Expand

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: 94664-82-1
(3S)-3-benzyloxycarbonylamino-4-hydroxybutanoic acid

Conditions

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran for 1h; Ambient temperature;	59%
Multi-step reaction with 2 steps 1: NaBH4 / tetrahydrofuran / 16 h / 20 °C 2: aq. CsCO3 / acetone / 3 h / 20 °C View Scheme

: 62-53-3
aniline

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

A: 30750-71-1
N-Benzyloxycarbonyl-L-asparaginsaeure-β-anilid

B: Cbz-Asp-anilide

Conditions

Conditions	Yield
With acetic acid In benzene for 0.166667h; Heating; Yields of byproduct given;	A n/a B 58%
In dimethyl sulfoxide for 0.333333h; Ambient temperature; Yield given. Yields of byproduct given;

...Expand

: 67688-72-6
4-aminomethyl-benzoic acid ; hydrochloride

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: 953435-25-1
(S)-4-((3-(benzyloxycarbonylamino)-2,5-dioxopyrrolidin-1-yl)methyl)benzoic acid

Conditions

Conditions	Yield
Stage #1: 4-aminomethyl-benzoic acid ; hydrochloride; N-benzyloxycarbonyl-L-aspartic acid anhydride With pyridine; triethylamine at 20℃; for 9h; Stage #2: With acetic acid at 83℃; for 24h;	56%

: 67-56-1
methanol

: 100-59-4
phenylmagnesium chloride

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

A: 35909-93-4
dimethyl (2S)-2-[(phenylmethoxy)carbonylamino]-butane-1,4-dioate

B: (3S)-methyl 3-(benzyloxycarbonylamino)-4-oxo-4-phenylbutanoate

Conditions

Conditions	Yield
Stage #1: phenylmagnesium chloride; N-benzyloxycarbonyl-L-aspartic acid anhydride In tetrahydrofuran at -78℃; for 4h; Stage #2: With citric acid In tetrahydrofuran at -78 - 20℃; Stage #3: methanol With thionyl chloride	A n/a B 54%

...Expand

: 67-56-1
methanol

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: 4668-42-2
(S)-2-benzyloxycarbonylamino-succinic acid 1-methyl ester

Conditions

Conditions	Yield
Stage #1: methanol; N-benzyloxycarbonyl-L-aspartic acid anhydride In ethyl acetate at 20℃; for 5h; Stage #2: With N-cyclohexyl-cyclohexanamine In di-isopropyl ether Stage #3: With hydrogenchloride In water; ethyl acetate pH=2;	54%

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: 1000278-32-9
N-benzyloxycarbonyl-L-aspartic acid thioanhydride

Conditions

Conditions	Yield
With sodium sulfide; tetrabutylammomium bromide In dichloromethane; water for 3h;	47%
With sodium sulfide; tetrabutylammomium bromide In dichloromethane; water for 3h;	47%

: 1-(2-aminoethyl)-3-(benzyloxy)-2-methylpyridin-4(1H)-one hydrochloride salt

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: (S)-4-((2-(3-(benzyloxy)-2-methyl-4-oxopyridin-1(4H)-yl)ethyl)amino)-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoic acid

Conditions

Conditions	Yield
Stage #1: 1-(2-aminoethyl)-3-(benzyloxy)-2-methylpyridin-4(1H)-one hydrochloride salt With potassium hydroxide In methanol for 1h; Inert atmosphere; Stage #2: N-benzyloxycarbonyl-L-aspartic acid anhydride In N,N-dimethyl-formamide at 59.84℃; for 3h; Inert atmosphere;	44%

: 67-56-1
methanol

: 693-03-8
n-butyl magnesium bromide

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

A: (S)-3-Benzyloxycarbonylamino-4-oxo-octanoic acid methyl ester

B: 35909-93-4
dimethyl (2S)-2-[(phenylmethoxy)carbonylamino]-butane-1,4-dioate

Conditions

Conditions	Yield
Stage #1: n-butyl magnesium bromide; N-benzyloxycarbonyl-L-aspartic acid anhydride In tetrahydrofuran at -78℃; for 4h; Stage #2: With citric acid In tetrahydrofuran at -78 - 20℃; Stage #3: methanol With thionyl chloride	A 41% B n/a

...Expand

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: 1-(3-aminopropyl)-3-(benzyloxy)-2-methylpyridin-4(1H)-one hydrochloride salt

: (S)-4-((3-(3-(benzyloxy)-2-methyl-4-oxopyridin-1(4H)-yl)propyl)amino)-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoic acid

Conditions

Conditions	Yield
Stage #1: 1-(3-aminopropyl)-3-(benzyloxy)-2-methylpyridin-4(1H)-one hydrochloride salt With potassium hydroxide In methanol for 1h; Inert atmosphere; Stage #2: N-benzyloxycarbonyl-L-aspartic acid anhydride In N,N-dimethyl-formamide at 59.84℃; for 3h; Inert atmosphere;	22%

: 2788-84-3
(S)-serine methyl ester

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: N-(N-benzyloxycarbonyl-L-α-aspartyl)-L-serine methyl ester

Conditions

Conditions	Yield
With chloroform

: 4070-48-8
L-Valine methyl ester

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: 159879-61-5
N-(N-benzyloxycarbonyl-L-α-aspartyl)-L-valine methyl ester

Conditions

Conditions	Yield
With ethyl acetate
With potassium hydrogencarbonate; ethyl acetate

: 4070-48-8
L-Valine methyl ester

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

A: 159879-61-5
N-(N-benzyloxycarbonyl-L-α-aspartyl)-L-valine methyl ester

B: 159879-62-6
N-(N-benzyloxycarbonyl-L-β-aspartyl)-L-valine methyl ester

Conditions

Conditions	Yield
With potassium hydrogencarbonate; ethyl acetate
With ethyl acetate

...Expand

: 16450-41-2
L-glutamic acid diethyl ester

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

A: N-(N-benzyloxycarbonyl-L-β-aspartyl)-L-glutamic acid diethyl ester

B: 112842-55-4
N-(N-benzyloxycarbonyl-L-α-aspartyl)-L-glutamic acid diethyl ester

Conditions

Conditions	Yield
With ethyl acetate

...Expand

: 5344-20-7
4-methyl pentanamine

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: 121790-47-4
L-aspartic acid isohexyl imide

Conditions

Conditions	Yield
at 130℃; Hydrieren des Reaktionsprodukts an Palladium/Kohle in Essigsaeure enthaltendem Aethanol;

(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate Chemical Properties

Molecular Structure of (S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate (CAS NO.4515-23-5):

IUPAC Name: benzyl N-(2,5-dioxooxolan-3-yl)carbamate
Empirical Formula: C₁₂H₁₁NO₅
Molecular Weight: 249.2194
H bond acceptors: 6
H bond donors: 1
Freely Rotating Bonds: 4
Polar Surface Area: 72.91 Å²
Index of Refraction: 1.57
Molar Refractivity: 59.95 cm³
Molar Volume: 181.8 cm³
Surface Tension: 55.7 dyne/cm
Density: 1.37 g/cm³
Flash Point: 250.3 °C
Enthalpy of Vaporization: 75.67 kJ/mol
Boiling Point: 490.2 °C at 760 mmHg
Vapour Pressure: 9.31E-10 mmHg at 25°C
Melting Point: 123-124 °C(lit.)
InChI
InChI=1/C12H11NO5/c14-10-6-9(11(15)18-10)13-12(16)17-7-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,13,16)
Smiles
O1C([C@@H](NC(=O)OCc2ccccc2)CC1=O)=O
EINECS: 224-838-3
Product Categories: N-CBZ; Aspartic Acid Derivatives; Peptide Synthesis; Unnatural Amino Acid Derivatives

(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate Safety Profile

WGK Germany: 3

(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate Specification

(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate , with CAS number of 4515-23-5, can be called N-Carbobenzyloxy-l-aspartic anhydride ; n-cbz-l-aspartic anhydride ; (s)-2-benzyloxycarbamylsuccinic anhydride ; (S)-benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate;N-Z-L-aspartic anhydride, 95% ; Carbamic acid, [(3S)-tetrahydro-2,5-dioxo-3-furanyl]-, phenylmethyl ester (9CI) ; (2,5-Dioxotetrahydrofuran-3β-yl)carbamic acid benzyl ester ; (2S)-2-(Benzyloxycarbonylamino)succinic anhydride .

Product Name

N-CARBOBENZYLOXY-L-ASPARTIC ANHYDRIDE

Synthetic route

(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate Chemical Properties

(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate Safety Profile

(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate Specification

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