Product Name

  • Name

    Z-PYR-OH

  • EINECS 250-936-0
  • CAS No. 32159-21-0
  • Article Data9
  • CAS DataBase
  • Density 1.408 g/cm3
  • Solubility
  • 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
  • Appearance
  • Safety 22-24/25
  • Risk Codes 22/22-36/37/38
  • Molecular Structure Molecular Structure of 32159-21-0 (Z-PYR-OH)
  • Hazard Symbols
  • 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;
  • PSA 83.91000
  • LogP 1.33670

Synthetic route

sodium carbonate
497-19-8

sodium carbonate

benzyl chloroformate
501-53-1

benzyl chloroformate

L-Pyroglutamic acid
98-79-3

L-Pyroglutamic acid

Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

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

benzyl chloroformate

L-Pyroglutamic acid
98-79-3

L-Pyroglutamic acid

Cbz-L-pGlu-OH
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;
N-benzyloxycarbonyl-L-glutamic acid
1155-62-0

N-benzyloxycarbonyl-L-glutamic acid

Cbz-L-pGlu-OH
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
N-(benzyloxycarbonyl)-L-glutamic acid anhydride
4124-76-9

N-(benzyloxycarbonyl)-L-glutamic acid anhydride

Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

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

2-bromothiophene

N-(benzyloxycarbonyl)-L-glutamic acid anhydride
4124-76-9

N-(benzyloxycarbonyl)-L-glutamic acid anhydride

A

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

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

B

N-benzyloxycarbonyl-L-glutamic acid
1155-62-0

N-benzyloxycarbonyl-L-glutamic acid

C

Cbz-L-pGlu-OH
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;
1-bromo-butane
109-65-9

1-bromo-butane

N-(benzyloxycarbonyl)-L-glutamic acid anhydride
4124-76-9

N-(benzyloxycarbonyl)-L-glutamic acid anhydride

A

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

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

B

N-benzyloxycarbonyl-L-glutamic acid
1155-62-0

N-benzyloxycarbonyl-L-glutamic acid

C

Cbz-L-pGlu-OH
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;
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

N-(benzyloxycarbonyl)-L-glutamic acid anhydride
4124-76-9

N-(benzyloxycarbonyl)-L-glutamic acid anhydride

A

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

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

B

N-benzyloxycarbonyl-L-glutamic acid
1155-62-0

N-benzyloxycarbonyl-L-glutamic acid

C

Cbz-L-pGlu-OH
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;
1-bromo-hexane
111-25-1

1-bromo-hexane

N-(benzyloxycarbonyl)-L-glutamic acid anhydride
4124-76-9

N-(benzyloxycarbonyl)-L-glutamic acid anhydride

A

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

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

B

N-benzyloxycarbonyl-L-glutamic acid
1155-62-0

N-benzyloxycarbonyl-L-glutamic acid

C

Cbz-L-pGlu-OH
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;
phenylmagnesium chloride
100-59-4

phenylmagnesium chloride

N-(benzyloxycarbonyl)-L-glutamic acid anhydride
4124-76-9

N-(benzyloxycarbonyl)-L-glutamic acid anhydride

A

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

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

B

N-benzyloxycarbonyl-L-glutamic acid
1155-62-0

N-benzyloxycarbonyl-L-glutamic acid

C

Cbz-L-pGlu-OH
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
phenyllithium
591-51-5

phenyllithium

N-(benzyloxycarbonyl)-L-glutamic acid anhydride
4124-76-9

N-(benzyloxycarbonyl)-L-glutamic acid anhydride

A

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

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

B

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

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

C

N-benzyloxycarbonyl-L-glutamic acid
1155-62-0

N-benzyloxycarbonyl-L-glutamic acid

D

Cbz-L-pGlu-OH
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
N-(benzyloxycarbonyl)-L-glutamic acid anhydride
4124-76-9

N-(benzyloxycarbonyl)-L-glutamic acid anhydride

A

N-benzyloxycarbonyl-L-glutamic acid
1155-62-0

N-benzyloxycarbonyl-L-glutamic acid

B

Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

Conditions
ConditionsYield
Stage #1: N-(benzyloxycarbonyl)-L-glutamic acid anhydride With tert-butylmagnesium chloride In tetrahydrofuran at -78℃; for 4h;
Stage #2: With citric acid In tetrahydrofuran
Stage #1: N-(benzyloxycarbonyl)-L-glutamic acid anhydride With phenylzinc chloride In tetrahydrofuran at -78℃; for 2h;
Stage #2: With citric acid In tetrahydrofuran
N-(benzyloxycarbonyl)-L-glutamic acid anhydride
4124-76-9

N-(benzyloxycarbonyl)-L-glutamic acid anhydride

Ph3MgLi

Ph3MgLi

A

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

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

B

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

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

C

N-benzyloxycarbonyl-L-glutamic acid
1155-62-0

N-benzyloxycarbonyl-L-glutamic acid

D

Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

Conditions
ConditionsYield
Stage #1: N-(benzyloxycarbonyl)-L-glutamic acid anhydride; Ph3MgLi In tetrahydrofuran at -78 - 20℃;
Stage #2: With citric acid In tetrahydrofuran
Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

methyl iodide
74-88-4

methyl iodide

(5S)-N-(benzyloxycarbonyl)-5-methoxycarbonyl-2-pyrrolidinone
75857-94-2

(5S)-N-(benzyloxycarbonyl)-5-methoxycarbonyl-2-pyrrolidinone

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane98%
With N-ethyl-N,N-diisopropylamine In dichloromethane for 6.5h; Heating / reflux;98%
(2R,4'R,8'R)-α-tocopheramine
3398-70-7

(2R,4'R,8'R)-α-tocopheramine

Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

A

vitamin E amine pyroglutamate conjugate

vitamin E amine pyroglutamate conjugate

B

N-methylmorpholine hydrochloride
3651-67-0

N-methylmorpholine hydrochloride

Conditions
ConditionsYield
Stage #1: Cbz-L-pGlu-OH With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at 0 - 20℃; for 2h;
Stage #2: (2R,4'R,8'R)-α-tocopheramine With triethylamine In tetrahydrofuran at 0℃;
A 98%
B n/a
VESA-PEG-NH2

VESA-PEG-NH2

Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

A

Reaxys ID: 11380187

Reaxys ID: 11380187

B

N-methylmorpholine hydrochloride
3651-67-0

N-methylmorpholine hydrochloride

Conditions
ConditionsYield
Stage #1: Cbz-L-pGlu-OH With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at 0 - 20℃; for 2h;
Stage #2: VESA-PEG-NH2 With triethylamine In tetrahydrofuran; water at 0℃;
A 98%
B n/a
tryptamine
61-54-1

tryptamine

Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

(S)-2-[2-(1H-Indol-3-yl)-ethylcarbamoyl]-5-oxo-pyrrolidine-1-carboxylic acid benzyl ester

(S)-2-[2-(1H-Indol-3-yl)-ethylcarbamoyl]-5-oxo-pyrrolidine-1-carboxylic acid benzyl ester

Conditions
ConditionsYield
In tetrahydrofuran Heating;90%
Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

benzyl chloride
100-44-7

benzyl chloride

dibenzyl (2S)-5-oxotetrahydro-1H-pyrrole-1,2-dicarboxylate
71389-33-8

dibenzyl (2S)-5-oxotetrahydro-1H-pyrrole-1,2-dicarboxylate

Conditions
ConditionsYield
With triethylamine In acetone for 72h; Heating;85%
Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

Z-Glp-NH2

Z-Glp-NH2

Conditions
ConditionsYield
With pyridine; di-tert-butyl dicarbonate; ammonium bicarbonate In 1,4-dioxane 4-16 h;84%
1,2,3-Benzotriazole
95-14-7

1,2,3-Benzotriazole

Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

benzyl (2S)-2-(1H-1,2,3-benzotriazol-1-ylcarbonyl)-5-oxotetrahydro-1H-pyrrole-1-carboxylate
958637-27-9

benzyl (2S)-2-(1H-1,2,3-benzotriazol-1-ylcarbonyl)-5-oxotetrahydro-1H-pyrrole-1-carboxylate

Conditions
ConditionsYield
Stage #1: 1,2,3-Benzotriazole With thionyl chloride In dichloromethane at 40 - 50℃; for 0.333333h;
Stage #2: Cbz-L-pGlu-OH In dichloromethane at 20℃; for 2h; Further stages.;
84%
Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

tert-butyl N-benzyloxycarbonyl-L-pyroglutamate
81470-51-1

tert-butyl N-benzyloxycarbonyl-L-pyroglutamate

Conditions
ConditionsYield
With perchloric acid In water at 20℃; for 16h;79%
Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

benzyl (2S)-2-[methyl(m-tolyl)carbamoyl]-5-oxopyrrolidine-1-carboxylate

benzyl (2S)-2-[methyl(m-tolyl)carbamoyl]-5-oxopyrrolidine-1-carboxylate

Conditions
ConditionsYield
With pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 20℃; for 12h;75%
8-amino quinoline
578-66-5

8-amino quinoline

Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

C22H19N3O4

C22H19N3O4

Conditions
ConditionsYield
Stage #1: Cbz-L-pGlu-OH With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at 0 - 20℃; for 1.5h;
Stage #2: 8-amino quinoline In tetrahydrofuran at 20℃; for 6h;
74%
Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

4-methoxy-aniline
104-94-9

4-methoxy-aniline

(S)-2-(4-Methoxy-phenylcarbamoyl)-5-oxo-pyrrolidine-1-carboxylic acid benzyl ester
339994-37-5

(S)-2-(4-Methoxy-phenylcarbamoyl)-5-oxo-pyrrolidine-1-carboxylic acid benzyl ester

Conditions
ConditionsYield
With 4-methyl-morpholine; chloroformic acid ethyl ester In ethyl acetate at -15 - 20℃; for 50h;68%
Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

Ala2-PheCH3, HBr
90427-75-1

Ala2-PheCH3, HBr

Z-Glp-Ala2-PheCH3
88576-78-7

Z-Glp-Ala2-PheCH3

Conditions
ConditionsYield
With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran67%
Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

isobutene
115-11-7

isobutene

tert-butyl N-benzyloxycarbonyl-L-pyroglutamate
81470-51-1

tert-butyl N-benzyloxycarbonyl-L-pyroglutamate

Conditions
ConditionsYield
With sulfuric acid In dichloromethane67%
Stage #1: Cbz-L-pGlu-OH; isobutene With sulfuric acid In dichloromethane at 20℃; Cooling with ice;
Stage #2: With sodium carbonate In dichloromethane; water
67%
With sulfuric acid In dichloromethane at 20℃; Cooling with ice;67%
With sulfuric acid In dichloromethane at 20℃; Cooling with ice;67%
Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

L-glutamic acid dibenzyl ester 4-toluenesulfonate
2791-84-6

L-glutamic acid dibenzyl ester 4-toluenesulfonate

Z-pGlu-Glu(OBzl)-OBzl
122389-55-3

Z-pGlu-Glu(OBzl)-OBzl

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane63%
Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

benzyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate
153870-19-0

benzyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: Cbz-L-pGlu-OH With 4-methyl-morpholine; chloroformic acid ethyl ester In tetrahydrofuran at -10℃;
Stage #2: With sodium tetrahydroborate In methanol at 0℃;
61%
Multi-step reaction with 2 steps
1: N-methyl morpholine / tetrahydrofuran / 0.08 h / -5 °C
2: NaBH4 / tetrahydrofuran
View Scheme
L-histidine methyl ester
95384-14-8

L-histidine methyl ester

Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

N-Z-L-pyroglutamyl-L-histidine methyl ester

N-Z-L-pyroglutamyl-L-histidine methyl ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide; acetonitrile 1h at -10 deg C, then 12h at 4 deg C;55%
Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

benzyl bromide
100-39-0

benzyl bromide

dibenzyl (2S)-5-oxotetrahydro-1H-pyrrole-1,2-dicarboxylate
71389-33-8

dibenzyl (2S)-5-oxotetrahydro-1H-pyrrole-1,2-dicarboxylate

Conditions
ConditionsYield
With potassium hydrogencarbonate In N,N-dimethyl-formamide for 18h; Ambient temperature;51%
Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

3-chloro-benzenecarboperoxoic acid
937-14-4

3-chloro-benzenecarboperoxoic acid

(R)-2-(3-Chloro-benzoyloxy)-5-oxo-pyrrolidine-1-carboxylic acid benzyl ester
130654-55-6

(R)-2-(3-Chloro-benzoyloxy)-5-oxo-pyrrolidine-1-carboxylic acid benzyl ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In chloroform at 25℃; for 1h;42%
Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

Ala3-PheCH3, HBr
90427-76-2

Ala3-PheCH3, HBr

Z-Glp-Ala3-PheCH3
88576-80-1

Z-Glp-Ala3-PheCH3

Conditions
ConditionsYield
With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran40%
BOC-glycine
4530-20-5

BOC-glycine

L-N-Boc-Ala
15761-38-3

L-N-Boc-Ala

N-Boc-O-benzyl-L-threonine
15260-10-3

N-Boc-O-benzyl-L-threonine

Boc-Arg(Tos)-OH
13836-37-8

Boc-Arg(Tos)-OH

BOC-O-benzyl-L-serine
23680-31-1

BOC-O-benzyl-L-serine

Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

Boc-Asp(O-cyclohexyl)-OH
73821-95-1

Boc-Asp(O-cyclohexyl)-OH

Boc-cysteine(4-Me-Bn)
61925-77-7

Boc-cysteine(4-Me-Bn)

Boc-(S)-Lys(2-Cl-Z)-OH
54613-99-9

Boc-(S)-Lys(2-Cl-Z)-OH

Nα-tert-butoxycarbonyl-1-formyl-L-tryptophan
47355-10-2

Nα-tert-butoxycarbonyl-1-formyl-L-tryptophan

N(α)-t-butoxycarbonyl-N(ϖ)-benzyloxymethyl-L-histidine
83468-83-1

N(α)-t-butoxycarbonyl-N(ϖ)-benzyloxymethyl-L-histidine

rerdused μ-conotoxin SIIIA

rerdused μ-conotoxin SIIIA

Conditions
ConditionsYield
Stage #1: Boc-cysteine(4-Me-Bn) With benzotriazol-1-ol In 1-methyl-pyrrolidin-2-one Automated synthesizer;
Stage #2: With trifluoroacetic acid
Stage #3: BOC-glycine; L-N-Boc-Ala; N-Boc-O-benzyl-L-threonine; Boc-Arg(Tos)-OH; BOC-O-benzyl-L-serine; Cbz-L-pGlu-OH; Boc-Asp(O-cyclohexyl)-OH; Boc-cysteine(4-Me-Bn); Boc-(S)-Lys(2-Cl-Z)-OH; Nα-tert-butoxycarbonyl-1-formyl-L-tryptophan; N(α)-t-butoxycarbonyl-N(ϖ)-benzyloxymethyl-L-histidine
22%
Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

N-benzyloxycarbonyl-L-glutamic acid-5-hydrazide
4510-09-2

N-benzyloxycarbonyl-L-glutamic acid-5-hydrazide

Conditions
ConditionsYield
With hydrazine hydrate
Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

benzylamine
100-46-9

benzylamine

N'-benzyl-N-benzyloxycarbonyl-L-glutamine
64153-27-1

N'-benzyl-N-benzyloxycarbonyl-L-glutamine

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

tert-butyl N-benzyloxycarbonyl-L-pyroglutamate
81470-51-1

tert-butyl N-benzyloxycarbonyl-L-pyroglutamate

Conditions
ConditionsYield
With perchloric acid Yield given. Multistep reaction;
With perchloric acid Ambient temperature; Yield given;
diethyl 1-aminoethylphosphonate
54788-35-1

diethyl 1-aminoethylphosphonate

Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

(S)-2-[1-(Diethoxy-phosphoryl)-ethylcarbamoyl]-5-oxo-pyrrolidine-1-carboxylic acid benzyl ester

(S)-2-[1-(Diethoxy-phosphoryl)-ethylcarbamoyl]-5-oxo-pyrrolidine-1-carboxylic acid benzyl ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 6.5h;
Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

L-tryptophan ethyl ester hydrochloride
2899-28-7, 6519-67-1, 61535-49-7, 67557-18-0, 68401-14-9

L-tryptophan ethyl ester hydrochloride

N-carbobenzoxy-L-pyroglutamyl-L-tryptophan ethyl ester
87694-59-5

N-carbobenzoxy-L-pyroglutamyl-L-tryptophan ethyl ester

Conditions
ConditionsYield
With chloroformic acid ethyl ester; triethylamine 1.) THF, 0 deg C, 30 min, 2.) r.t., 3 h; Yield given. Multistep reaction;
Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

tert.-butyloxycarbonylalanyl-Nε-benzyloxycarbonyllysyl-serine methyl ester
84983-67-5

tert.-butyloxycarbonylalanyl-Nε-benzyloxycarbonyllysyl-serine methyl ester

Z-Pyr-Ala-Lys(Z)-Ser-OMe
84983-68-6

Z-Pyr-Ala-Lys(Z)-Ser-OMe

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; methoxybenzene; trifluoroacetic acid 1.) room temperature, 20 min 2.) DMF, 0 deg C, overnight, 4 deg C; Yield given. Multistep reaction;
Cbz-L-pGlu-OH
32159-21-0

Cbz-L-pGlu-OH

HCl.H-Leu-Gly-NH2
38173-66-9

HCl.H-Leu-Gly-NH2

(Z)--Leu-Gly-NH2
39705-62-9

(Z)--Leu-Gly-NH2

Conditions
ConditionsYield
With 4-methyl-morpholine; triethylamine; isobutyl chloroformate 1.) THF, -20 deg C, 10 min, 2.) THF, DMF, H2O, RT, 1 h; Yield given. Multistep reaction;

(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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