Conditions | Yield |
---|---|
With water for 16h; Heating; | 95% |
In water for 16h; Heating; | 95% |
With 1,1'-carbonyldiimidazole In chloroform at 55℃; for 3h; Solvent; Concentration; | 76.8% |
L-N-t-butoxycarbonylpyroglutamic acid
L-Pyroglutamic acid
Conditions | Yield |
---|---|
With silica gel In dichloromethane for 0.0166667h; Irradiation; | 91% |
With tin(II) trifluoromethanesulfonate In dichloromethane at 20℃; for 2h; | 87% |
tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate
L-Pyroglutamic acid
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane for 0.333333h; Ambient temperature; | 90% |
Conditions | Yield |
---|---|
With triethylamine In water; N,N-dimethyl-formamide at 40℃; for 20h; | 88.3% |
(5S)-2,2-bis(trifluoromethyl)-1-aza-3-oxabicyclo[3.3.0]octan-4,8-dione
L-Pyroglutamic acid
Conditions | Yield |
---|---|
With water In isopropyl alcohol at 20℃; | 87% |
Conditions | Yield |
---|---|
at 175℃; under 3750.38 Torr; for 5h; Temperature; Pressure; Autoclave; Large scale; | A 15.9% B 83% |
Boc-Gln-OH
trifluoroacetic acid
A
L-glutamic acid
B
L-Pyroglutamic acid
Conditions | Yield |
---|---|
at 20℃; for 0.25h; | A 61% B 18% |
tert-butyl (4S,4'S,5'R)-4-amino-5-(3',4'-dimethyl-2'-oxo-5'-phenyl-1'-imidazolydinyl)-5-oxopentanoate
L-Pyroglutamic acid
Conditions | Yield |
---|---|
With water for 12h; Hydrolysis; cyclization; Heating; | 45% |
L-glutamic acid γ-benzyl ester
A
benzaldehyde
B
benzoic acid
C
L-Pyroglutamic acid
D
benzyl alcohol
Conditions | Yield |
---|---|
With sodium hydroxide; sodium tetrachloropalladate(II) In water Product distribution; Ambient temperature; initial pH:6.8; variation of initial pH and temperature; | A 37% B 4% C n/a D 24% |
H-Glu(OChp)-OH
L-Pyroglutamic acid
Conditions | Yield |
---|---|
With triethylamine In water; N,N-dimethyl-formamide at 40℃; for 20h; | 4.1% |
Conditions | Yield |
---|---|
With water |
Conditions | Yield |
---|---|
With ammonium hydroxide |
diethyl 2-aminopentanedioate
L-Pyroglutamic acid
Conditions | Yield |
---|---|
With water |
L-glutamic acid diethyl ester
L-Pyroglutamic acid
Conditions | Yield |
---|---|
With water |
Conditions | Yield |
---|---|
With palladium on activated charcoal; acetic acid Hydrogenation; |
Conditions | Yield |
---|---|
at 28℃; for 840h; pH=5.5 (acetate buffer), PhCH3 on surface; | |
With human blood serum at 24.84℃; |
(S)-2-Amino-pentanedioic acid 5-ethyl ester
A
ethanol
B
L-Pyroglutamic acid
Conditions | Yield |
---|---|
In water at 40℃; Rate constant; pH 7.6-10.4, μ=0.5 (KCl); |
histrelin
A
His-Trp-Ser-Tyr-(D-Nim-bzl-His)-Leu-Arg-Pro-NHEt
C
Ser-Tyr-(D-Nim-bzl-His)-Leu-Arg-Pro-NHEt
E
L-Pyroglutamic acid
Conditions | Yield |
---|---|
With water at 87℃; for 432h; Product distribution; degradation, var. reaction time, temperature and ph; |
N-Acetylpyroglutamic acid
A
N-Acetyl-D-pyroglutamic acid
B
L-Pyroglutamic acid
Conditions | Yield |
---|---|
With potassium hydroxide; potassium phosphate buffer; porcine kidney acylase I at 40℃; relative initial rate of hydrolysis, also with Aspergillus acylase I as a catalyst; |
Conditions | Yield |
---|---|
With water In acetonitrile at 40℃; Rate constant; pH 9.7-10.5, μ=0.5 (KCl); | |
With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid; lipase from Bacillus thermocatenulanatus In water at 40℃; pH=7.20; Enzyme kinetics; |
L-Pyroglutamic acid
Conditions | Yield |
---|---|
With Quinine |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 67 percent / dimethylsulfoxide / 20 °C 2: 99 percent / SOCl2; DMF / CH2Cl2 / 20 °C 3: 87 percent / H2O / propan-2-ol / 20 °C View Scheme |
(S)-[2,2-bis(trifluoromethyl)-5-oxo-1,3-oxazolidin-4-yl]propionic acid
A
L-Pyroglutamic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 99 percent / SOCl2; DMF / CH2Cl2 / 20 °C 2: 87 percent / H2O / propan-2-ol / 20 °C View Scheme |
N-Boc-L-proline
L-Pyroglutamic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: dicyclohexylcarbodiimide, 4-dimethylaminopyridine 2: 95 percent / RuO2 hydrate, 10percent aqueous NaIO4 / ethyl acetate / 2 h / Ambient temperature 3: 90 percent / CF3COOH / CH2Cl2 / 0.33 h / Ambient temperature View Scheme |
N-BOC-proline tert-butyl ester
L-Pyroglutamic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 95 percent / RuO2 hydrate, 10percent aqueous NaIO4 / ethyl acetate / 2 h / Ambient temperature 2: 90 percent / CF3COOH / CH2Cl2 / 0.33 h / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 75 percent / dicyclohexylcarbodiimide, 4-dimethylaminopyridine / tetrahydrofuran 2: 76 percent / H2, AcOH / Pd / methanol / 24 h 3: 4.1 percent / Et3N / dimethylformamide; H2O / 20 h / 40 °C View Scheme |
C26H48N6O15
A
5-O-(5-amino-5-deoxy-β-D-ribofuranosyl)-1-N-[(S)-4-amino-2-hydroxy-butanoyl]paromamine
B
L-Pyroglutamic acid
Conditions | Yield |
---|---|
BtrG enzyme In water at 20℃; for 24h; Product distribution / selectivity; HEPES buffer; Enzymatic reaction; |
diazomethane
L-Pyroglutamic acid
methyl (S)-pyroglutamate
Conditions | Yield |
---|---|
In diethyl ether | 100% |
With diethyl ether | |
In methanol; diethyl ether at 0℃; for 0.5h; |
Conditions | Yield |
---|---|
With thionyl chloride at 0 - 25℃; | 100% |
With methanesulfonic acid In chloroform; water Reflux; | 100% |
With Dowex-50W (X8-200) resin Inert atmosphere; Reflux; | 100% |
acetic acid tert-butyl ester
L-Pyroglutamic acid
L-t-butyl pyroglutamate
Conditions | Yield |
---|---|
With perchloric acid In water at 20℃; for 18h; | 100% |
Stage #1: acetic acid tert-butyl ester; L-Pyroglutamic acid With perchloric acid at 20℃; for 48h; Inert atmosphere; Stage #2: With perchloric acid for 48h; Inert atmosphere; | 90% |
With perchloric acid at 20℃; for 96h; Inert atmosphere; | 90% |
1,1,1,3,3,3-hexamethyl-disilazane
L-Pyroglutamic acid
L-trimethylsilyl pyroglutamate
Conditions | Yield |
---|---|
With saccharin for 2.5h; Heating; | 100% |
Conditions | Yield |
---|---|
With triethylamine In 1,2-dichloro-ethane at 60℃; for 15h; Temperature; Large scale; | 100% |
With triethylamine In acetone for 168h; Heating; | 85% |
With TEA In acetone | 85% |
2-methyl-1-buten-4-ol
L-Pyroglutamic acid
(5S)-2-pyrrolidone-5-carboxylic acid 3-methyl-3-butenyl ester
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; | 100% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene at 130℃; for 2h; Dean-Stark; | 100% |
With toluene-4-sulfonic acid In benzene for 2h; Heating; |
L-Pyroglutamic acid
pyroglutamoyl chloride
Conditions | Yield |
---|---|
Stage #1: L-Pyroglutamic acid With 1,1,1,3,3,3-hexamethyl-disilazane; saccharin for 2.5h; Heating / reflux; Stage #2: With oxalyl dichloride In dichloromethane at 20℃; Heating / reflux; | 100% |
p-toluenesulfonyl chloride
L-Pyroglutamic acid
(S)-toluene-4-sulfonic acid 5-oxo-pyrrolidin-2-ylmethyl ester
Conditions | Yield |
---|---|
Stage #1: L-Pyroglutamic acid With thionyl chloride In methanol at 20℃; for 4h; Stage #2: With sodium tetrahydroborate In ethanol at 20℃; for 15h; Stage #3: p-toluenesulfonyl chloride With dmap; triethylamine In dichloromethane at 20℃; for 16h; | 100% |
Conditions | Yield |
---|---|
In methanol; chloroform Molecular sieve; Reflux; | 100% |
Conditions | Yield |
---|---|
In methanol | 100% |
Conditions | Yield |
---|---|
With thionyl chloride at 0 - 20℃; | 99% |
With thionyl chloride at 0℃; for 15h; | 99% |
With thionyl chloride at -5 - 20℃; for 10h; | 98% |
Conditions | Yield |
---|---|
With ammonium peroxydisulfate; silver nitrate In water at 20℃; for 2h; Reagent/catalyst; Temperature; | 99% |
With iodosylbenzene In dichloromethane for 48h; Ambient temperature; | 27% |
allyl alcohol
L-Pyroglutamic acid
(S)-allyl 5-oxopyrrolidine-2-carboxylate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane | 99% |
With thionyl chloride at 20℃; for 12h; | 85% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 5℃; Inert atmosphere; |
L-Pyroglutamic acid
Conditions | Yield |
---|---|
With triethylamine; HATU In N,N-dimethyl-formamide at 20℃; for 18h; | 99% |
tegaserod
L-Pyroglutamic acid
Conditions | Yield |
---|---|
In acetone at 25 - 55℃; for 20h; | 98.3% |
isopropyl alcohol
L-Pyroglutamic acid
(S)-isopropyl 5-oxopyrrolidine-2-carboxylate
Conditions | Yield |
---|---|
With thionyl chloride at 15℃; for 2h; | 98.1% |
With toluene-4-sulfonic acid for 6h; Haller-Bauer Reaction; 4 A molecular sieve; | 96% |
With toluene-4-sulfonic acid for 6h; Heating / reflux; | 96% |
(1S,2R,5S)-(+)-menthol
L-Pyroglutamic acid
(S)-[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyl] 2-oxopyrrolidine-5-carboxylate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 0 - 23℃; for 24.5h; Inert atmosphere; | 98% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 20.5h; Inert atmosphere; | 86% |
Conditions | Yield |
---|---|
In ethanol at 25℃; for 0.5h; | 98% |
2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine
L-Pyroglutamic acid
amlodipine (R)-(+)-pyroglutamate
Conditions | Yield |
---|---|
In ethanol at 5 - 20℃; for 1h; | 97.1% |
Conditions | Yield |
---|---|
In water for 2h; Heating; | 97% |
methyl glyoxylate methyl hemi-acetal
L-Pyroglutamic acid
methyl 2-hydroxy-2-(2-oxoprolin-1-yl)acetate
Conditions | Yield |
---|---|
In acetone for 60h; Heating; | 97% |
Conditions | Yield |
---|---|
In ethanol at 20℃; for 1h; | 97% |
di-tert-butyl dicarbonate
L-Pyroglutamic acid
(2S,5R)-6-(sulfoxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide
Conditions | Yield |
---|---|
Stage #1: L-Pyroglutamic acid With benzyl chloride; triethylamine In chloroform at 0℃; for 3.5h; Reflux; Stage #2: di-tert-butyl dicarbonate With dmap; triethylamine In ethyl acetate at -25 - 35℃; for 4.91667h; Stage #3: With pyrographite; sodium sulfate In cyclohexane; water Solvent; Temperature; | 96.3% |
Conditions | Yield |
---|---|
With sulfuric acid In dichloromethane | 96% |
With sulfuric acid In dichloromethane at 0 - 20℃; Inert atmosphere; | 78% |
With sulfuric acid In dichloromethane at 25℃; for 48h; | 65% |
Conditions | Yield |
---|---|
With thionyl chloride; N,N-dimethyl-formamide for 15h; Ambient temperature; | 96% |
With thionyl chloride at 0 - 20℃; | 96% |
With thionyl chloride; N,N-dimethyl-formamide at 20℃; | 90% |
(S)-benzyl 2-((S)-2-(2-amino-3-(3-((S)-2-(benzyloxycarbonylamino)-3-tert-butoxy-3-oxopropyl)-2-(triethylsilyl)-1H-indol-6-yl)-4-methylpentanamido)-4-methylpentanamido)-3-methylbutanoate
L-Pyroglutamic acid
(S)-benzyl 2-((S)-2-(2-amino-3-(3-((S)-2-(benzyloxycarbonylamino)-3-tert-butoxy-3-oxopropyl)-2-(triethylsilyl)-1H-indol-6-yl)-4-methyl-2-((S)-5-oxopyrrolilidine-2-carboxamido)pentanamido)-4-methylpentanamido)-3-methylbutanoate
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 0℃; for 8h; | 96% |
Conditions | Yield |
---|---|
In acetone at 20 - 25℃; for 4h; Solvent; | 96% |
vortioxetine
L-Pyroglutamic acid
Conditions | Yield |
---|---|
In isopropyl alcohol at 20 - 60℃; for 2h; | 96% |
2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-6-methyl-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester
L-Pyroglutamic acid
Conditions | Yield |
---|---|
In ethyl acetate at 25℃; for 1h; | 95.3% |
In ethyl acetate at 25℃; for 1h; | 95.3% |
The IUPAC name of L-Pyroglutamic acid is (2S)-5-oxopyrrolidine-2-carboxylic acid. With the CAS registry number 98-79-3, it is also named as 2-Benzothiazolesulfenemorpholide. The product's categories are Heterocycles; Pyrrolidine Series; Chiral; Pyroglutamic Acid [Pyr, pGu]; Unusual Amino Acids; Amino Acids; Biochemistry; Biological-modified Amino Acids; for Resolution of Bases; Optical Resolution; Synthetic Organic Chemistry; Amino Acids; Nutraceuticals, and the other registry numbers are 16891-48-8; 29222-42-2; 312618-42-1; 35255-51-7; 498-91-9; 6886-28-8; 87430-62-4. Besides, it is white to light yellow crystal powder, which should be stored in a cool, dry, well ventilated warehouse away from fire and heat source. And the packaging must be sealed and not damp. In addition, this chemical is stable, and incompatible with bases, acids, strong oxidizing agents.
Physical properties about L-Pyroglutamic acid are: (1)ACD/LogP: -1.348; (2)ACD/LogD (pH 5.5): -3.38; (3)ACD/LogD (pH 7.4): -4.88; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 4; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.512 ; (12)Molar Refractivity: 28.033 cm3; (13)Molar Volume: 93.496 cm3; (14)Polarizability: 11.113 10-24cm3; (15)Surface Tension: 54.6319999694824 dyne/cm; (16)Density: 1.381 g/cm3; (17)Flash Point: 227.848 °C; (18)Enthalpy of Vaporization: 78.09 kJ/mol; (19)Boiling Point: 453.134 °C at 760 mmHg
Preparation and Uses of L-Pyroglutamic acid: Please heat 42 % Glutamic acid solution for 3 hours at 140 °C. And you will obtain the reaction liquid that is the main component of L-Pyroglutamic acid. After decompression and concentration, crystallization, washing, drying, you will get the product. The yield is 94 %. Furthermore, this chemical is used as intermediate of organic synthesis, food additives. It is also used in biochemical study, medicine, cosmetics and other industries. Additionally, it is used as resolving agent.
When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. You should wear suitable protective clothing, gloves and eye/face protection. Moreover, in case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1;
(2)InChIKey=ODHCTXKNWHHXJC-VKHMYHEASA-N;
(3)Smiles[C@@H]1(NC(=O)CC1)C(=O)O
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rat | LD50 | oral | > 1gm/kg (1000mg/kg) | United States Patent Document. Vol. #4882359, | |
rat | LD50 | subcutaneous | > 2gm/kg (2000mg/kg) | United States Patent Document. Vol. #4882359, |
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