98-79-3

Basic information

• Product Name: L-Pyroglutamic acid
• Synonyms: 5-OXO-L-PROLINE;5-oxoproline;5-OXO-2-PYRROLIDINECARBOXYLIC ACID;L-GLUTIMINIC ACID;L-GLUTAMIC ACID LACTAM;(-)-L-PYROGLUTAMIC ACID;L-PYROGLUTAMIC ACID;L-2-PYRROLIDONE-5-CARBOXYLIC ACID
• CAS NO: 98-79-3
• Molecular Formula: C₅H₇NO₃
• Molecular Weight: 129.11
• EINECS: 202-700-3
• Product Categories: 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;Amino acid
• Mol File: 98-79-3.mol
• Article Data: 64

Chemical Properties

• Melting Point: 160-163 °C(lit.)
• Boiling Point: 239.15°C (rough estimate)
• Flash Point: 227.8 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.3816 (rough estimate)
• Vapor Pressure: 1.79E-09mmHg at 25°C
• Refractive Index: -10 ° (C=5, H2O)
• Storage Temp.: Store at RT.
• Solubility: H2O: 1 M at 20 °C, clear, colorless
• PKA: 3.32(at 25℃)
• Water Solubility: 10-15 g/100 mL (20 ºC)
• Stability: Stable. Incompatible with bases, acids, strong oxidizing agents.
• Merck: 14,8001
• BRN: 82132
• CAS DataBase Reference: L-Pyroglutamic acid(CAS DataBase Reference)
• NIST Chemistry Reference: L-Pyroglutamic acid(98-79-3)
• EPA Substance Registry System: L-Pyroglutamic acid(98-79-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: TW3710000
• F: 21
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 98-79-3(Hazardous Substances Data)

Usage

Characteristics and Application

L-pyroglutamic acid is an amino acid that occurs naturally in the body. It is present in the brain, spinal fluid, skin and blood.pyroglutamic acid is one of the major components of natural moisturizing factor of the skin, its moisturizing ability is far stronger than glycerin and propylene glycol. Moreover, it is non-toxic, non-irritating, and is an excellent raw material for modern skin care, and hair care cosmetics. Pyroglutamic acid also has inhibitory effect on the tyrosine oxidase activity, and thus preventing "melanoidins" substance from being deposited in the skin, and having a whitening effect on the skin. It has a keratin softening effect which can be used in nail cosmetics.In addition to be applied in cosmetics, L-pyroglutamic acid derivatives can also have reaction with a number of other organic compounds for synthesis of derivatives. It also has some special effect on the surface activity and brilliant effect. Moreover, it can also be used as surfactants for detergents; as a chemical reagent, it can be used for the resolution of racemic amines; it can also be used as a kind of organic intermediates.

Pyroglutamic acid

Pyroglutamic acid is a kind of based 5-oxo-proline. It is produced by the dehydration and formation of intramolecular amide bond between the α-NH2 group and γ-hydroxy of glutamic acid; the molecule can also be produced from glutamine by losing its intramolecular amine group. The condition of glutathione synthetase deficiency can cause the anemia of pyroglutamic acid with a series of clinical symptoms. Pyroglutamic acid anemia is a kind of organic acid metabolic disorder disease caused by glutathione synthetase hyperlipidemia. Clinical manifestations: disease onset occurs within 12 to 24 hours of born with progressive hemolysis, jaundice, chronic metabolic acidosis, mental retardation; urine containing pyroglutamic acid, lactic acid, α-deoxy-4-hydroxyphenyl acetyl acid lactone. For treatment, based on the actual symptoms, pay attention to adjust the diet after yearling.

Preparation

L-pyroglutamic acid is formed by removing one intramolecular water molecule in the L-glutamic acid; the preparation process is simple with the key step being the control of the temperature and dehydration time. (1) Add100 g of L-glutamic acid into a 500-ml beaker; heat the beaker in an oil bath until the temperature was raised to 145~150 °C, incubate for 45 minutes to perform dehydration reaction. The dehydrated solution was brown. (2) After the end of dehydration reaction, pour the solution into a volume of about 350 ml of boiling water with a solution of all further being dissolved in water. Cool to 40~50 °C, add appropriate amount of activated carbon for decolorization (repeated twice) to obtain a colorless transparent solution. (3) directly heat and evaporate the colorless and transparent solution of the step (2) is a colorless and transparent solution for concentration to a half of the previous volume and then continue for concentration in a water bath to a volume of about 1/3 of the previous solution, and then stop heating; have it slightly cooled in the hot water bath for crystallization; the colorless prisms can be obtained after 10 to 20 hours. The applied amount of L-pyroglutamic acid in cosmetics should depend on the formula. This product can also be applied to cosmetic in the form of 50% concentrated solution.

Chemical Properties

It is colorless crystals with the melting point being 162-163 °C; it is soluble in water, alcohol, acetone and acetic acid, slightly soluble in ethyl acetate, but insoluble in ether.

Uses

L-Pyroglutamic acid is used in the synthesis of:Nonproteinogenic amino acids such as (3S,4R)-3,4-dimethyl-L-pyroglutamic acid and (3S,4R)-3,4-dimethyl-L-glutamine.Chiral N-heterocyclic carbenes (NHCs) as catalysts for the asymmetric dimerization of alkylarylketenes to give the corresponding α-quaternary β-alkylidenyl-β-lactones.It is also used in the total synthesis of (?)-stemoamide and celogentin C.It can be used as a kind of intermediates of organic synthesis as well as food additives.It is used in food, medicine, cosmetics and other industries.

Production method

There are semi-synthetic methods, enzymatic conversion method and total synthesis method. Currently the major approach of industrial production is the semi-synthetic method with glutamic acid being the raw material. Have the 42% of glutamic acid solution heated at 140 °C for 3h to obtain the reaction solution with L-pyroglutamic acid being the major component. The reaction solution further undergoes concentration under reduced pressure, crystallization, washing, and drying to obtain the L-pyroglutamic acid with the conversion rate being 94%.

Chemical Properties

L-pyroglutamic acid has its scientific name being L-2-pyrrolidone-5-carboxylic acid. Precipitation from ethanol and petroleum ether mixture were colorless orthorhombic bipyramid crystals with the melting temperature being 162~163 °C. It is soluble in water, alcohol, acetone and acetic acid, slightly soluble in ethyl acetate, and insoluble in ether. Specific rotation-11.9 ° (c = 2, H2O). It is produced from 42% aqueous solution of glutamic acid which subjects to heating dehydration, concentration, crystallization, washing and drying to obtain L-pyroglutamic acid.

Uses

L-Pyroglutamic acid is an amino acid that is used in the synthesis of peptides. It has also been observed to convert when placed at the N-terminus in vivo to create IgG2 antibodies.

Uses

A building block for pharmaceuticals and asymmetric synthesis

Uses

In the resolution of racemic amines.

Definition

ChEBI: An optically active form of 5-oxoproline having L-configuration.

Flammability and Explosibility

Notclassified

Purification Methods

Crystallise S-pyroglutamic acid by dissolving it in boiling EtOH (20g in 100mL), cooling and after a few minutes additing pet ether (b 40-60o, 120mL), then after 5 minutes adding a further 120mL, and coThis has m 155.5-157.5o and [] D -11.4o (c 4.4, H2O) [Hardy Synthesis 290 1978, Pellegata et al. Synthesis 614 1978]. The NH4 salt has m 184-186o (from EtOH). [Beilstein 22/6 V 7.]

InChI:InChI=1/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/p-1/t3-/m0/s1

Synthetic route

L-glutamic acid (56-86-0) → L-Pyroglutamic acid (98-79-3)

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 (53100-44-0) → L-Pyroglutamic acid (98-79-3)

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 (91229-91-3) → L-Pyroglutamic acid (98-79-3)

Conditions	Yield
With trifluoroacetic acid In dichloromethane for 0.333333h; Ambient temperature;	90%

L-glutamic acid γ-benzyl ester (1676-73-9) → L-Pyroglutamic acid (98-79-3)

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 (317845-09-3) → L-Pyroglutamic acid (98-79-3)

Conditions	Yield
With water In isopropyl alcohol at 20℃;	87%

L-glutamic acid (56-86-0) → Pyroglutamic acid (149-87-1) + L-Pyroglutamic acid (98-79-3)

Conditions	Yield
at 175℃; under 3750.38 Torr; for 5h; Temperature; Pressure; Autoclave; Large scale;	A 15.9% B 83%

Boc-Gln-OH (13726-85-7) + trifluoroacetic acid (76-05-1) → L-glutamic acid (56-86-0) + L-Pyroglutamic acid (98-79-3)

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 (220280-79-5) → L-Pyroglutamic acid (98-79-3)

Conditions	Yield
With water for 12h; Hydrolysis; cyclization; Heating;	45%

L-glutamic acid γ-benzyl ester (1676-73-9) → benzaldehyde (100-52-7) + benzoic acid (65-85-0) + L-Pyroglutamic acid (98-79-3) + benzyl alcohol (100-51-6)

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 (107930-17-6) → L-Pyroglutamic acid (98-79-3)

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide at 40℃; for 20h;	4.1%

D-Glutamic acid (6893-26-1) → L-Pyroglutamic acid (98-79-3)

Conditions	Yield
With water

(S)-2-Amino-pentanedioic acid 5-ethyl ester (1119-33-1) → L-Pyroglutamic acid (98-79-3)

Conditions	Yield
With ammonium hydroxide

diethyl 2-aminopentanedioate (55895-85-7) → L-Pyroglutamic acid (98-79-3)

Conditions	Yield
With water

L-glutamic acid diethyl ester (16450-41-2) → L-Pyroglutamic acid (98-79-3)

Conditions	Yield
With water

N-(benzyloxycarbonyl)-L-glutamic acid anhydride (4124-76-9) → L-Pyroglutamic acid (98-79-3)

Conditions	Yield
With palladium on activated charcoal; acetic acid Hydrogenation;

L-glutamine (56-85-9) → L-Pyroglutamic acid (98-79-3)

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 (1119-33-1) → ethanol (64-17-5) + L-Pyroglutamic acid (98-79-3)

Conditions	Yield
In water at 40℃; Rate constant; pH 7.6-10.4, μ=0.5 (KCl);

histrelin (76712-82-8) → His-Trp-Ser-Tyr-(D-Nim-bzl-His)-Leu-Arg-Pro-NHEt (134190-11-7) + cyclo(-His-Trp) + Ser-Tyr-(D-Nim-bzl-His)-Leu-Arg-Pro-NHEt (134009-09-9) + 35925-21-4 + L-Pyroglutamic acid (98-79-3)

Conditions	Yield
With water at 87℃; for 432h; Product distribution; degradation, var. reaction time, temperature and ph;

N-Acetylpyroglutamic acid (53971-11-2) → N-Acetyl-D-pyroglutamic acid (53971-11-2, 56805-18-6, 89885-76-7) + L-Pyroglutamic acid (98-79-3)

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;

ethyl (S)-pyroglutamate (7149-65-7) → ethanol (64-17-5) + L-Pyroglutamic acid (98-79-3)

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;

inactive form → L-Pyroglutamic acid (98-79-3)

Conditions	Yield
With Quinine

L-glutamic acid (56-86-0) → L-Pyroglutamic acid (98-79-3) + Fmoc-Pro-Rink amide-MBHA resin

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 (131021-88-0) → L-Pyroglutamic acid (98-79-3) + Fmoc-Pro-Rink amide-MBHA resin

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 (15761-39-4) → L-Pyroglutamic acid (98-79-3)

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 (91237-84-2) → L-Pyroglutamic acid (98-79-3)

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

Cbz-(L)-Glu-OBn (3705-42-8) → L-Pyroglutamic acid (98-79-3) + natrium carbonate

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 (1134188-65-0) → 5-O-(5-amino-5-deoxy-β-D-ribofuranosyl)-1-N-[(S)-4-amino-2-hydroxy-butanoyl]paromamine (1134188-60-5) + L-Pyroglutamic acid (98-79-3)

Conditions	Yield
BtrG enzyme In water at 20℃; for 24h; Product distribution / selectivity; HEPES buffer; Enzymatic reaction;

diazomethane (186581-53-3, 908094-01-9) + L-Pyroglutamic acid (98-79-3) → methyl (S)-pyroglutamate (4931-66-2)

Conditions	Yield
In diethyl ether	100%
With diethyl ether
In methanol; diethyl ether at 0℃; for 0.5h;

methanol (67-56-1) + L-Pyroglutamic acid (98-79-3) → methyl (S)-pyroglutamate (4931-66-2)

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 (540-88-5) + L-Pyroglutamic acid (98-79-3) → L-t-butyl pyroglutamate (35418-16-7, 85136-12-5)

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 (999-97-3) + L-Pyroglutamic acid (98-79-3) → L-trimethylsilyl pyroglutamate (97717-45-8)

Conditions	Yield
With saccharin for 2.5h; Heating;	100%

benzyl chloride (100-44-7) + L-Pyroglutamic acid (98-79-3) → benzyl (L)-pyroglutamate (94885-52-6)

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 (763-32-6) + L-Pyroglutamic acid (98-79-3) → (5S)-2-pyrrolidone-5-carboxylic acid 3-methyl-3-butenyl ester (865183-91-1)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;	100%
With dmap; dicyclohexyl-carbodiimide In dichloromethane

2-(Trimethylsilyl)ethanol (2916-68-9) + L-Pyroglutamic acid (98-79-3) → 2-(trimethylsilyl)ethyl (S)-5-oxopyrrolidine-2-carboxylate

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 (98-79-3) → pyroglutamoyl chloride (55478-53-0)

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 (98-59-9) + L-Pyroglutamic acid (98-79-3) → (S)-toluene-4-sulfonic acid 5-oxo-pyrrolidin-2-ylmethyl ester (51693-17-5)

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%

methanesulfonic acid (75-75-2) + L-Pyroglutamic acid (98-79-3) → methyl (S)-pyroglutamate (4931-66-2)

Conditions	Yield
In methanol; chloroform Molecular sieve; Reflux;	100%

sodium methylate (124-41-4) + L-Pyroglutamic acid (98-79-3) → 5-methoxypyrrolidin-2-one

Conditions	Yield
In methanol	100%

ethanol (64-17-5) + L-Pyroglutamic acid (98-79-3) → ethyl (S)-pyroglutamate (7149-65-7)

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%

L-Pyroglutamic acid (98-79-3) → Succinimide (123-56-8)

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 (107-18-6) + L-Pyroglutamic acid (98-79-3) → (S)-allyl 5-oxopyrrolidine-2-carboxylate (4931-79-7)

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;

N1-(4,4-difluorocyclohexyl)-4-(3,5-dimethylisoxazol-4-yl)benzene-1,2-diamine + L-Pyroglutamic acid (98-79-3) → (S)-N-(2-((4,4-difluorocyclohexyl)amino)-5-(3,5-dimethylisoxazol-4-yl)phenyl)-5-oxopyrrolidine-2-carboxamide

Conditions	Yield
With triethylamine; HATU In N,N-dimethyl-formamide at 20℃; for 18h;	99%

tegaserod (1044642-88-7) + L-Pyroglutamic acid (98-79-3) → 3-(5-methoxy-1H-indol-3-ylmethylene)-N-pentylcarbazimidamide pidolate

Conditions	Yield
In acetone at 25 - 55℃; for 20h;	98.3%

isopropyl alcohol (67-63-0) + L-Pyroglutamic acid (98-79-3) → (S)-isopropyl 5-oxopyrrolidine-2-carboxylate (52989-50-1)

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 (15356-60-2) + L-Pyroglutamic acid (98-79-3) → (S)-[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyl] 2-oxopyrrolidine-5-carboxylate (139014-48-5)

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%

carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3) + L-Pyroglutamic acid (98-79-3) → C16H34NO2(1+)*C5H6NO3(1-)

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 (88150-42-9) + L-Pyroglutamic acid (98-79-3) → amlodipine (R)-(+)-pyroglutamate (663180-17-4)

Conditions	Yield
In ethanol at 5 - 20℃; for 1h;	97.1%

L-Pyroglutamic acid (98-79-3) + LiOH → lithium L-pyroglutamate (38609-04-0)

Conditions	Yield
In water for 2h; Heating;	97%

methyl glyoxylate methyl hemi-acetal (109745-70-2, 19757-97-2) + L-Pyroglutamic acid (98-79-3) → methyl 2-hydroxy-2-(2-oxoprolin-1-yl)acetate (502481-82-5)

Conditions	Yield
In acetone for 60h; Heating;	97%

amlodipine (103129-82-4) + L-Pyroglutamic acid (98-79-3) → (S)-(-)-amlodipine pidolate salt (851447-24-0)

Conditions	Yield
In ethanol at 20℃; for 1h;	97%

di-tert-butyl dicarbonate (24424-99-5) + L-Pyroglutamic acid (98-79-3) → (2S,5R)-6-(sulfoxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide (1192500-31-4)

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%

isobutene (115-11-7) + L-Pyroglutamic acid (98-79-3) → L-t-butyl pyroglutamate (35418-16-7, 85136-12-5)

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%

L-Pyroglutamic acid (98-79-3) + benzyl alcohol (100-51-6) → benzyl (L)-pyroglutamate (94885-52-6)

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 (1189587-53-8) + L-Pyroglutamic acid (98-79-3) → (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 (1189587-54-9)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 0℃; for 8h;	96%

febuxostat + L-Pyroglutamic acid (98-79-3) → febuxostat hemipidolate salt

Conditions	Yield
In acetone at 20 - 25℃; for 4h; Solvent;	96%

vortioxetine (508233-74-7) + L-Pyroglutamic acid (98-79-3) → 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine L-pyroglutamate

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 (113994-41-5) + L-Pyroglutamic acid (98-79-3) → amlodipine (S)-(-)-pyroglutamate

Conditions	Yield
In ethyl acetate at 25℃; for 1h;	95.3%
In ethyl acetate at 25℃; for 1h;	95.3%

Upstream product

• 98792-93-9 2,4',6'-Trichloro-6-phenyl-4,5'-bipyrimidine 
• 98792-90-6 4,6(1H,5H)-Pyrimidinedione, 5-acetyldihydro- (9CI) 
• 98792-82-6 2-Butenamide, 2-cyano-3-hydroxy-, (Z)- (9CI) 
• 98792-81-5 5-Acetyl-6-hydroxy-4(1H)-pyrimidinone 
• 98792-64-4 2-(6-AMINO-BENZOOXAZOL-2-YL)-PHENOL 
• 98792-03-1 1-CHLORO-6-METHOXY-9H-2,4,9-TRIAZA-FLUORENE 
• 98792-02-0 1-CHLORO-9H-2,4,9-TRIAZA-FLUORENE 
• 98791-67-4 R(+)-BAY K 8644 
• 98791-58-3 1-hydroxy-11-deoxycarminomycin II 
• 98791-45-8 1,2,6,7-TETRAHYDRODICYCLOPENTA[CD,JK]PYRENE 
• 98791-43-6 DICYCLOPENTA[CD,JK]PYRENE 
• 98790-49-9 benzyldimethyllaurylammonium 
• 98789-52-7 O,O-dimethyl O-[3-methyl-2,4-bis(methylsulfanyl)phenyl] phosphorothioate 
• 98789-52-7 O,O-dimethyl O-[3-methyl-2,4-bis(methylsulfanyl)phenyl] phosphorothioate 

Downstream Products

• 98793-15-8 Cyclopentanol, 2-(2-pyridinylthio)-, trans- (9CI) 
• 98793-83-0 2-(acetyloxy)-N-[3-[3-(1-piperidinyl-methyl)phenoxy]propyl]- acetamide monohydrochloride 
• 987-94-0 (3ALPHA)-URS-12-ENE-3,28-DIOL 
• 98795-78-9 2,6-dimethoxy-4-(piperidin-1-ylcarbonyl)phenol 
• 98795-79-0 2,6-dimethoxy-4-[(4-methylpiperazin-1-yl)carbonyl]phenol hydrochloride 
• 98795-83-6 2-[2,6-dimethoxy-4-(morpholin-4-ylcarbonyl)phenoxy]-N,N-dimethylethanamine ethanedioate 
• 98795-88-1 N-{4-[2-(diethylamino)ethoxy]phenyl}pyridine-3-carboxamide hydrochloride 
• 98795-90-5 N,N-diethyl-2-{4-[(3,4,5-trimethoxybenzoyl)amino]phenoxy}ethanaminium chloride 
• 98795-91-6 1-{[4-(benzyloxy)-3,5-dimethoxyphenyl]carbonyl}-4-methylpiperazine hydrochloride 
• 98795-93-8 Pyrrolidine, 1-(3,5-dimethoxy-4-(2-(dimethylamino)ethoxy)benzoyl)-, et hanedioate (1:1) 
• 98795-94-9 2-[2,6-dimethoxy-4-(piperidin-1-ylcarbonyl)phenoxy]-N,N-dimethylethanamine ethanedioate 
• 98795-95-0 N-(4-(2-(Diethylamino)ethoxy)phenyl)-3,4,5-trimethoxybenzenemethanamin e dihydrochloride 
• 98796-09-9 3(2H)-Pyridazinone, 4-chloro-2-methyl-5-(methylamino)- 
• 98796-15-7 3(2H)-Pyridazinone, 4-chloro-2-ethyl-5-(methylamino)- 

Recommend Products

• 6893-26-1  D-Glutamic acid 
• 56-86-0  L-glutamic acid 
• 1119-33-1  (S)-2-Amino-pentanedioic acid 5-ethyl ester 
• 55895-85-7  diethyl 2-aminopentanedioate 
• 16450-41-2  L-glutamic acid diethyl ester 
• 4931-66-2  methyl (S)-pyroglutamate 
• 186581-53-3  diazomethane 
• 16473-66-8  L-(+)-1,1'-methylenebis[5-oxo-2-pyrrolidinecarboxylic acid] 
• 50-00-0  formaldehyd 
• 3081-62-7  N-(γ-glutamyl)methylamine 
• 74-89-5  methylamine 
• 110-88-3  1,3,5-Trioxan 
• 56-85-9  L-glutamine 
• 64-17-5  ethanol