Product Name

  • Name

    (S)-BENZYL 2-AZETIDINONE-4-CARBOXYLATE

  • EINECS
  • CAS No. 72776-05-7
  • Article Data17
  • CAS DataBase
  • Density 1.268 g/cm3
  • Solubility Soluble in water
  • Melting Point 137-140 °C(lit.)
  • Formula C11H11 N O3
  • Boiling Point 404.7 °C at 760 mmHg
  • Molecular Weight 205.213
  • Flash Point 198.5 °C
  • Transport Information
  • Appearance white to light yellow crystalline powder
  • Safety 24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 72776-05-7 ((S)-BENZYL 2-AZETIDINONE-4-CARBOXYLATE)
  • Hazard Symbols
  • Synonyms 2-Azetidinecarboxylicacid, 4-oxo-, phenylmethyl ester, (S)-; Benzyl (S)-4-oxo-2-azetidinecarboxylate
  • PSA 55.40000
  • LogP 0.94710

Synthetic route

dibenzyl L-aspartate
2791-79-9

dibenzyl L-aspartate

(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

Conditions
ConditionsYield
Stage #1: dibenzyl L-aspartate With chloro-trimethyl-silane; triethylamine In diethyl ether at 0℃; for 1h;
Stage #2: With tert-butylmagnesium chloride In diethyl ether at -5 - 0℃; for 2h;		47%
Stage #1: dibenzyl L-aspartate With chloro-trimethyl-silane In diethyl ether at -78 - 25℃;
Stage #2: With tert-butylmagnesium bromide In diethyl ether at -78 - 25℃;		40%
With chloro-trimethyl-silane; tert-butylmagnesium chloride
(L)-N-(trimethylsilyl)dibenzyl aspartate
72776-06-8

(L)-N-(trimethylsilyl)dibenzyl aspartate

(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

Conditions
ConditionsYield
With tert-butylmagnesium chloride In diethyl ether at 0℃; Yield given;
With tert-butylmagnesium chloride 1.) 0 deg C, 2.) room temperature, overnight; Yield given;
With tert-butylmagnesium chloride In diethyl ether at 0℃;
With tert-butylmagnesium chloride In diethyl ether at -5 - 20℃; for 12.5h;5.1 g
D-aspartic acid dibenzyl ester
4079-59-8

D-aspartic acid dibenzyl ester

(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

Conditions
ConditionsYield
With chloro-trimethyl-silane; tert-butylmagnesium bromide; triethylamine Yield given. Multistep reaction;
dibenzyl L-aspartate
2791-79-9

dibenzyl L-aspartate

methoxy poly(ethylene glycol) sodium salt

methoxy poly(ethylene glycol) sodium salt

(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: TEA; 4-dimethylaminopyridine / diethyl ether / 3 h / 0 °C
2: 5.1 g / tBuMgCl / diethyl ether / 12.5 h / -5 - 20 °C
View Scheme
C16H21NO5

C16H21NO5

(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

Conditions
ConditionsYield
With cytochrome P411 expressed in Escherichia coli In aq. phosphate buffer at 20℃; for 24h; pH=8; Catalytic behavior; Enzymatic reaction; enantioselective reaction;n/a
(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

(S)-4-(hydroxymethyl)-2-azetidinone
72776-07-9

(S)-4-(hydroxymethyl)-2-azetidinone

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0 - 20℃; Inert atmosphere;100%
With sodium tetrahydroborate In methanol71%
With sodium tetrahydroborate In methanol
With lithium borohydride
(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

α-benzyl-L-aspartic acid poly(β-peptide); Monomer(s): α-benzyl-L-aspartic acid β-lactam

α-benzyl-L-aspartic acid poly(β-peptide); Monomer(s): α-benzyl-L-aspartic acid β-lactam

Conditions
ConditionsYield
With magnesium bis(hexamethyldisilazide) In dichloromethane for 0.2h; Product distribution; Further Variations:; Reagents; Solvents; concentrations;100%
With magnesium bis(hexamethyldisilazide) In dichloromethane for 0.2h;100%
(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

(S)-4-oxo-azetidine-2-carboxylic acid
16404-94-7

(S)-4-oxo-azetidine-2-carboxylic acid

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In tetrahydrofuran for 14h;98%
With hydrogen; palladium 10% on activated carbon In methanol at 25℃; under 760.051 Torr; for 0.5h;93%
With hydrogen; palladium on activated charcoal In isopropyl alcohol at 20℃; under 1140.08 Torr; for 0.333333h;85%
With hydrogen; palladium on activated charcoal In tetrahydrofuran at 25℃; for 0.75h;11.8 g
(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(S)-benzyl-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate
82938-49-6

(S)-benzyl-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate

Conditions
ConditionsYield
With triethylamine98%
With triethylamine97%
With triethylamine In N,N-dimethyl-formamide93%
(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

(S)-4-Oxo-azetidine-2-carboxylic acid 2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethyl ester
372515-10-1

(S)-4-Oxo-azetidine-2-carboxylic acid 2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethyl ester

α-3,6,9,12-tetraoxatridecyl-L-aspartic acid, α-benzyl-L-aspartic acid diblock copoly(β-peptide); Monomer(s): α-3,6,9,12-tetraoxatridecyl-L-aspartic acid β-lactam; α-benzyl-L-aspartic acid β-lactam

α-3,6,9,12-tetraoxatridecyl-L-aspartic acid, α-benzyl-L-aspartic acid diblock copoly(β-peptide); Monomer(s): α-3,6,9,12-tetraoxatridecyl-L-aspartic acid β-lactam; α-benzyl-L-aspartic acid β-lactam

Conditions
ConditionsYield
With tris(bistrimethylsilylamine)scandium(III) In dichloromethane at 20℃;95%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

(4S)-benzyl N-(tbutoxycarbonyl)-azetidin-2-one-4-carboxylate

(4S)-benzyl N-(tbutoxycarbonyl)-azetidin-2-one-4-carboxylate

Conditions
ConditionsYield
With dmap In acetonitrile for 17h; Ambient temperature;94%
(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

ortho-toluoyl chloride
933-88-0

ortho-toluoyl chloride

benzyl (S)-1-(2-methylbenzoyl)-4-oxoazetidine-2-carboxylate

benzyl (S)-1-(2-methylbenzoyl)-4-oxoazetidine-2-carboxylate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;86%
1,1,1,2,2,2-hexamethyldisilane
1450-14-2

1,1,1,2,2,2-hexamethyldisilane

(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

(4S)-N-(trimethylsilyl)-2-oxoazetidine-4-carboxylic acid benzyl ester
100188-43-0

(4S)-N-(trimethylsilyl)-2-oxoazetidine-4-carboxylic acid benzyl ester

Conditions
ConditionsYield
With saccharin In 1,2-dimethoxyethane for 2h; Heating;78%
2,2-dimethyl-propanol-1
75-84-3

2,2-dimethyl-propanol-1

(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

(S)-4-(2,2'-dimethyl)propoxycarbonyl-2-azetidinone

(S)-4-(2,2'-dimethyl)propoxycarbonyl-2-azetidinone

Conditions
ConditionsYield
With tetrabutoxytitanium at 100℃; for 2h;75%
(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

2-tolyl isocyanate
614-68-6

2-tolyl isocyanate

benzyl (S)-4-oxo-(o-tolylcarbamoyl)azetidine-2-carboxylate

benzyl (S)-4-oxo-(o-tolylcarbamoyl)azetidine-2-carboxylate

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 2h; Inert atmosphere;75%
phosgene
75-44-5

phosgene

(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

benzyl (S)-4-oxo-1-(phenylcarbamoyl)azetidine-2-carboxylate
911852-27-2

benzyl (S)-4-oxo-1-(phenylcarbamoyl)azetidine-2-carboxylate

Conditions
ConditionsYield
Stage #1: phosgene; aniline With triethylamine In dichloromethane; toluene at 0℃; for 0.5h;
Stage #2: (S)-benzyl 4-oxoazetidine-2-carboxylate In tetrahydrofuran; dichloromethane; toluene		73%
(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

BOC-L-alanine-NCA
125814-30-4

BOC-L-alanine-NCA

benzyl (S)-1-[(S)-N-(tert-butoxycarbonyl)-alanyl]-4-oxoazetidine-2-carboxylate
321863-81-4

benzyl (S)-1-[(S)-N-(tert-butoxycarbonyl)-alanyl]-4-oxoazetidine-2-carboxylate

Conditions
ConditionsYield
Stage #1: (S)-benzyl 4-oxoazetidine-2-carboxylate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h;
Stage #2: BOC-L-alanine-NCA In tetrahydrofuran; hexane at -78℃; for 1h;		71%
(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

butan-1-ol
71-36-3

butan-1-ol

(S)-4-butoxycarbonyl-2-azetidinone

(S)-4-butoxycarbonyl-2-azetidinone

Conditions
ConditionsYield
With tetrabutoxytitanium at 100℃; for 2h;69%
(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

2,6-dimethyl-4-pyrimidinyl p-toluenesulfonate
40227-86-9

2,6-dimethyl-4-pyrimidinyl p-toluenesulfonate

(R)-benzyl 1-(2,6-dimethylpyrimidin-4-yl)-4-oxoazetidine-2-carboxylate
1233503-36-0

(R)-benzyl 1-(2,6-dimethylpyrimidin-4-yl)-4-oxoazetidine-2-carboxylate

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; potassium carbonate; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;69%
(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

isopropyl alcohol
67-63-0

isopropyl alcohol

(S)-4-isopropoxycarbonyl-2-azetidinone
155878-39-0

(S)-4-isopropoxycarbonyl-2-azetidinone

Conditions
ConditionsYield
With tetrabutoxytitanium at 205℃; for 2h;68%
methanol
67-56-1

methanol

(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

methyl (S)-(-)-2-oxoazetidine-4-carboxylate
100188-44-1

methyl (S)-(-)-2-oxoazetidine-4-carboxylate

Conditions
ConditionsYield
With tetrabutoxytitanium at 86℃; for 4h;64%
(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

Benzyl bromoacetate
5437-45-6

Benzyl bromoacetate

benzyl (S)-1-[(benzyloxycarbonyl)methyl]-4-oxoazetidine-2-carboxylate

benzyl (S)-1-[(benzyloxycarbonyl)methyl]-4-oxoazetidine-2-carboxylate

Conditions
ConditionsYield
Stage #1: (S)-benzyl 4-oxoazetidine-2-carboxylate With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at -78℃; for 0.0333333h;
Stage #2: Benzyl bromoacetate In tetrahydrofuran; hexane at -78 - 20℃;		59%
octanol
111-87-5

octanol

(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

(S)-4-octoxycarbonyl-2-azetidinone

(S)-4-octoxycarbonyl-2-azetidinone

Conditions
ConditionsYield
With tetrabutoxytitanium at 80℃; for 2h;58%
2-methyl-propan-1-ol
78-83-1

2-methyl-propan-1-ol

(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

2-methyl-1-propyl (S)-(-)-2-oxoazetidine-4-carboxylate
120260-62-0

2-methyl-1-propyl (S)-(-)-2-oxoazetidine-4-carboxylate

Conditions
ConditionsYield
With tetrabutoxytitanium at 85℃; for 2h;58%
With tetrabutoxytitanium
1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

(S)-4-dodecoxycarbonyl-2-azetidinone

(S)-4-dodecoxycarbonyl-2-azetidinone

Conditions
ConditionsYield
With tetrabutoxytitanium at 105℃; for 4h;58%
Cyclopentanol
96-41-3

Cyclopentanol

(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

(S)-4-cyclopentoxycarbonyl-2-azetidinone

(S)-4-cyclopentoxycarbonyl-2-azetidinone

Conditions
ConditionsYield
With tetrabutoxytitanium at 85℃; for 2h;56%
(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

cyclohexanol
108-93-0

cyclohexanol

(S)-4-cyclohexoxycarbonyl-2-azetidinone

(S)-4-cyclohexoxycarbonyl-2-azetidinone

Conditions
ConditionsYield
With tetrabutoxytitanium at 105℃; for 3h;56%
1-octadecanol
112-92-5

1-octadecanol

(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

(S)-4-octadecoxycarbonyl-2-azetidinone

(S)-4-octadecoxycarbonyl-2-azetidinone

Conditions
ConditionsYield
With tetrabutoxytitanium at 91℃; for 4h;51%
(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

hexan-1-ol
111-27-3

hexan-1-ol

(S)-4-hexoxycarbonyl-2-azetidinone

(S)-4-hexoxycarbonyl-2-azetidinone

Conditions
ConditionsYield
With tetrabutoxytitanium at 85℃; for 2h;47%
(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

4-isopropyl-2,5-dioxo-oxazolidine-3-carboxylic acid-tert-butyl ester
141468-55-5

4-isopropyl-2,5-dioxo-oxazolidine-3-carboxylic acid-tert-butyl ester

benzyl (S)-1-[(S)-N-(tert-butoxycarbonyl)-valyl]-4-oxoazetidine-2-carboxylate

benzyl (S)-1-[(S)-N-(tert-butoxycarbonyl)-valyl]-4-oxoazetidine-2-carboxylate

Conditions
ConditionsYield
Stage #1: (S)-benzyl 4-oxoazetidine-2-carboxylate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h;
Stage #2: 4-isopropyl-2,5-dioxo-oxazolidine-3-carboxylic acid-tert-butyl ester In tetrahydrofuran; hexane at -78℃; for 1h;		41%
(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

Z-L-Ala-NCA

Z-L-Ala-NCA

benzyl (S)-1-[(S)-N-(benzyloxycarbonyl)-alanyl]-4-oxoazetidine-2-carboxylate

benzyl (S)-1-[(S)-N-(benzyloxycarbonyl)-alanyl]-4-oxoazetidine-2-carboxylate

Conditions
ConditionsYield
Stage #1: (S)-benzyl 4-oxoazetidine-2-carboxylate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h;
Stage #2: Z-L-Ala-NCA In tetrahydrofuran; hexane at -78℃; for 1h;		37%
tert-butyl(4-(isocyanatomethyl)phenyl)carbamate

tert-butyl(4-(isocyanatomethyl)phenyl)carbamate

(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

benzyl (S)-1-(4-tert-butoxycarbonylaminobenzylcarbamoyl)-4-oxoazetidine-2-carboxylate

benzyl (S)-1-(4-tert-butoxycarbonylaminobenzylcarbamoyl)-4-oxoazetidine-2-carboxylate

Conditions
ConditionsYield
Stage #1: (S)-benzyl 4-oxoazetidine-2-carboxylate With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.25h; Inert atmosphere;
Stage #2: tert-butyl(4-(isocyanatomethyl)phenyl)carbamate In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;		37%
(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

tert-butyl 2-(fluorocarbonyl)pyrrolidine-1-carboxylate
133010-05-6

tert-butyl 2-(fluorocarbonyl)pyrrolidine-1-carboxylate

benzyl N-[N-(tert-butoxycarbonyl)-prolyl]-4-oxoazetidine-2-carboxylate

benzyl N-[N-(tert-butoxycarbonyl)-prolyl]-4-oxoazetidine-2-carboxylate

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃;20%

(S)-Benzyl 2-azetidinone-4-carboxylate Chemical Properties

IUPAC Name: Benzyl (2S)-4-oxoazetidine-2-carboxylate
Synonyms of (S)-Benzyl 2-azetidinone-4-carboxylate (CAS NO.72776-05-7): Benzyl (2S)-4-oxoazetidine-2-carboxylate ; Benzyl (S)-4-oxo-2-azetidinecarboxylate
CAS NO: 72776-05-7
Molecular Formula: C11H11NO3
Molecular Weight: 205.21
Molecular Structure:
H bond acceptors: 4
H bond donors: 1
Freely Rotating Bonds: 4
Polar Surface Area: 46.61 Å2
Index of Refraction: 1.565
Molar Refractivity: 52.75 cm3
Molar Volume: 161.8 cm3
Surface Tension: 50.4 dyne/cm
Density: 1.268 g/cm3
Flash Point: 198.5 °C
Enthalpy of Vaporization: 65.62 kJ/mol
Boiling Point: 404.7 °C at 760 mmHg
Vapour Pressure: 9.28E-07 mmHg at 25°C
Melting Point: 1137-140 °C(lit.)
Alpha : -42.5 º (C=3, CHCL3)
Storage temp: 0-6°C
Appearance: (S)-Benzyl 2-azetidinone-4-carboxylate (CAS NO.72776-05-7) is white to light yellow crystal powder.
SMILES: O=C(OCc1ccccc1)[C@H]2NC(=O)C2 
InChI: InChI=1/C11H11NO3/c13-10-6-9(12-10)11(14)15-7-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,12,13)/t9-/m0/s1
InChIKey: WGLLBHSIXLWVFU-VIFPVBQEBT
Std. InChI: InChI=1S/C11H11NO3/c13-10-6-9(12-10)11(14)15-7-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,12,13)/t9-/m0/s1
Std. InChIKey: WGLLBHSIXLWVFU-VIFPVBQESA-N
Product Categories: chiral;Chiral Building Blocks;Lactams;Organic Building Blocks

(S)-Benzyl 2-azetidinone-4-carboxylate Safety Profile

Safety Statements: 24/25
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3

(S)-Benzyl 2-azetidinone-4-carboxylate Specification

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam. 
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Store (S)-Benzyl 2-azetidinone-4-carboxylate (CAS NO.72776-05-7) in a cool, dry place. Store in a tightly closed container. Keep refrigerated. (Store below 4°C/39°F.) Store protected from light.

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