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(S)-1-(Benzyloxycarbonyl)-5-oxopyrrolidine-2-carboxylic acid
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Name

(S)-1-(Benzyloxycarbonyl)-5-oxopyrrolidine-2-carboxylic acid

 EINECS 250-936-0
CAS No. 32159-21-0 Density 1.408 g/cm3
PSA 83.91000 LogP 1.33670
Solubility N/A Melting Point 128-130 °C
Formula C13H13NO5 Boiling Point 525.4 °C at 760 mmHg
Molecular Weight 263.25 Flash Point 271.5 °C
Transport Information N/A Appearance N/A
Safety 22-24/25 Risk Codes 22/22-36/37/38
Molecular Structure Molecular Structure of 32159-21-0 (Z-PYR-OH) Hazard Symbols N/A
Synonyms

1,2-Pyrrolidinedicarboxylicacid, 5-oxo-, 1-(phenylmethyl) ester, (S)-;1,2-Pyrrolidinedicarboxylic acid,5-oxo-, 1-benzyl ester, L- (8CI);(2S)-5-Oxopyrrolidine-1,2-dicarboxylic acid1-benzyl ester;(Benzyloxycarbonyl)-L-pyroglutamic acid;Carbobenzoxy-L-pyroglutamic acid;L-(Phenylmethoxycarbonyl)pyroglutamic acid;N-Benzyloxycarbonyl-L-pyroglutamic acid;N-Benzyloxycarbonylpyroglutamic acid;N-Carbobenzoxypyroglutamic acid;Z-Pyr-OH;

Article Data 9

(S)-1-(Benzyloxycarbonyl)-5-oxopyrrolidine-2-carboxylic acid Synthetic route

497-19-8

sodium carbonate

501-53-1

benzyl chloroformate

98-79-3

L-Pyroglutamic acid

32159-21-0

Cbz-L-pGlu-OH

Conditions
ConditionsYield
In 1,4-dioxane; sodium hydroxide87%
501-53-1

benzyl chloroformate

98-79-3

L-Pyroglutamic acid

32159-21-0

Cbz-L-pGlu-OH

Conditions
ConditionsYield
With triethylamine In acetonitrile for 1h; Ambient temperature;20%
With 2,2,2-trifluoro-N,N-bis(trimethylsilyl)-acetamide; acetonitrile; methyloxirane 1.) r.t., 15 min, 2.) 1 h; Yield given. Multistep reaction;
1155-62-0

N-benzyloxycarbonyl-L-glutamic acid

32159-21-0

Cbz-L-pGlu-OH

Conditions
ConditionsYield
With N-cyclohexyl-cyclohexanamine; dicyclohexyl-carbodiimide 1.) THF, 0 deg C; Multistep reaction;
Yield given. Multistep reaction;
Multi-step reaction with 2 steps
1: DCC / tetrahydrofuran / 0 °C
2: dicyclohexylamine (DCHA) / tetrahydrofuran / 0 °C
View Scheme
4124-76-9

N-(benzyloxycarbonyl)-L-glutamic acid anhydride

32159-21-0

Cbz-L-pGlu-OH

Conditions
ConditionsYield
With N-cyclohexyl-cyclohexanamine In tetrahydrofuran at 0℃; Yield given;
1003-09-4

2-bromothiophene

4124-76-9

N-(benzyloxycarbonyl)-L-glutamic acid anhydride

A

(S)-4-Benzyloxycarbonylamino-5-oxo-5-thiophen-2-yl-pentanoic acid

B

1155-62-0

N-benzyloxycarbonyl-L-glutamic acid

C

32159-21-0

Cbz-L-pGlu-OH

Conditions
ConditionsYield
Stage #1: 2-bromothiophene With magnesium In tetrahydrofuran at 40℃; for 2h;
Stage #2: N-(benzyloxycarbonyl)-L-glutamic acid anhydride In tetrahydrofuran at -78℃; for 4h;
Stage #3: With citric acid In tetrahydrofuran at -78 - 20℃; Title compound not separated from byproducts;
109-65-9

1-bromo-butane

4124-76-9

N-(benzyloxycarbonyl)-L-glutamic acid anhydride

A

(S)-4-Benzyloxycarbonylamino-5-oxo-nonanoic acid

B

1155-62-0

N-benzyloxycarbonyl-L-glutamic acid

C

32159-21-0

Cbz-L-pGlu-OH

Conditions
ConditionsYield
Stage #1: 1-bromo-butane With magnesium In tetrahydrofuran at 40℃; for 2h;
Stage #2: N-(benzyloxycarbonyl)-L-glutamic acid anhydride In tetrahydrofuran at -78℃; for 4h;
Stage #3: With citric acid In tetrahydrofuran at -78 - 20℃; Title compound not separated from byproducts;
2398-37-0

3-methoxyphenyl bromide

4124-76-9

N-(benzyloxycarbonyl)-L-glutamic acid anhydride

A

(S)-4-Benzyloxycarbonylamino-5-(3-methoxy-phenyl)-5-oxo-pentanoic acid

B

1155-62-0

N-benzyloxycarbonyl-L-glutamic acid

C

32159-21-0

Cbz-L-pGlu-OH

Conditions
ConditionsYield
Stage #1: 3-methoxyphenyl bromide With magnesium In tetrahydrofuran at 40℃; for 2h;
Stage #2: N-(benzyloxycarbonyl)-L-glutamic acid anhydride In tetrahydrofuran at -78℃; for 4h;
Stage #3: With citric acid In tetrahydrofuran at -78 - 20℃; Title compound not separated from byproducts;
111-25-1

1-bromo-hexane

4124-76-9

N-(benzyloxycarbonyl)-L-glutamic acid anhydride

A

(S)-4-Benzyloxycarbonylamino-5-oxo-undecanoic acid

B

1155-62-0

N-benzyloxycarbonyl-L-glutamic acid

C

32159-21-0

Cbz-L-pGlu-OH

Conditions
ConditionsYield
Stage #1: 1-bromo-hexane With magnesium In tetrahydrofuran at 40℃; for 2h;
Stage #2: N-(benzyloxycarbonyl)-L-glutamic acid anhydride In tetrahydrofuran at -78℃; for 4h;
Stage #3: With citric acid In tetrahydrofuran at -78 - 20℃; Title compound not separated from byproducts;
100-59-4

phenylmagnesium chloride

4124-76-9

N-(benzyloxycarbonyl)-L-glutamic acid anhydride

A

(S)-4-Benzyloxycarbonylamino-5-oxo-5-phenyl-pentanoic acid

B

1155-62-0

N-benzyloxycarbonyl-L-glutamic acid

C

32159-21-0

Cbz-L-pGlu-OH

Conditions
ConditionsYield
Stage #1: phenylmagnesium chloride; N-(benzyloxycarbonyl)-L-glutamic acid anhydride In tetrahydrofuran at -78℃; for 4h;
Stage #2: With citric acid In tetrahydrofuran
591-51-5

phenyllithium

4124-76-9

N-(benzyloxycarbonyl)-L-glutamic acid anhydride

A

(S)-2-Benzyloxycarbonylamino-5-oxo-5-phenyl-pentanoic acid

B

(S)-4-Benzyloxycarbonylamino-5-oxo-5-phenyl-pentanoic acid

C

1155-62-0

N-benzyloxycarbonyl-L-glutamic acid

D

32159-21-0

Cbz-L-pGlu-OH

Conditions
ConditionsYield
Stage #1: phenyllithium; N-(benzyloxycarbonyl)-L-glutamic acid anhydride In tetrahydrofuran at -78℃; for 4h;
Stage #2: With citric acid In tetrahydrofuran
...Expand

(S)-1-(Benzyloxycarbonyl)-5-oxopyrrolidine-2-carboxylic acid Chemical Properties

IUPAC Name: 5-Oxo-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid
Synonyms of N(alpha)-Carbobenzoxypyroglutamic acid  (CAS NO.32159-21-0): 1-[(Benzyloxy)carbonyl]-5-oxoproline ; 1,2-Pyrrolidinedicarboxylic acid,5-oxo-,1-(phenylmethyl) ester,(S)- ; 1-Benzyl hydrogen (S)-5-oxopyrrolidine-1,2-dicarboxylate ; (S)-1-(Benzyloxycarbonyl)-5-oxopyrrolidine-2-carboxylic acid
CAS NO: 32159-21-0
Molecular Formula: C13H13NO5
Molecular Weight: 263.246
Molecular Structure:
EINECS: 250-936-0
H bond acceptors: 6
H bond donors: 1
Freely Rotating Bonds: 4
Polar Surface Area: 72.91 Å2
Index of Refraction: 1.597
Molar Refractivity: 63.68 cm3
Molar Volume: 186.8 cm3
Surface Tension: 65.6 dyne/cm
Density: 1.408 g/cm3
Flash Point: 271.5 °C
Enthalpy of Vaporization: 84.16 kJ/mol
Boiling Point: 525.4 °C at 760 mmHg
Vapour Pressure: 7.26E-12 mmHg at 25°C
Melting Point: 128-130°C
Storage temp: -20°C
SMILES: O=C2N(C(=O)OCc1ccccc1)C(C(=O)O)CC2
InChI: InChI=1/C13H13NO5/c15-11-7-6-10(12(16)17)14(11)13(18)19-8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H,16,17)
InChIKey: VHSFUGXCSGOKJX-UHFFFAOYAB
Std. InChI: InChI=1S/C13H13NO5/c15-11-7-6-10(12(16)17)14(11)13(18)19-8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H,16,17)
Std. InChIKey: VHSFUGXCSGOKJX-UHFFFAOYSA-N
Product Categories of N(alpha)-Carbobenzoxypyroglutamic acid  (CAS NO.32159-21-0): pharmacetical;Pyroglutamic acid [Pyr, pGu];Unusual Amino Acids;Z-Amino acid series;Amino Acids;I - Z;Modified Amino Acids

(S)-1-(Benzyloxycarbonyl)-5-oxopyrrolidine-2-carboxylic acid Safety Profile

Safety Statements: 22-24/25
S22: Do not breathe dust. 
S24/25: When N(alpha)-Carbobenzoxypyroglutamic acid  (CAS NO.32159-21-0) is used,avoid contact with skin and eyes.
WGK Germany: 3

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