ethanol
(S,S)-1,7-diazatricyclo[7.3.0.07,11]dodecane-2,6,8,12-tetrone
ethyl (S)-pyroglutamate
Conditions | Yield |
---|---|
With potassium cyanide for 4h; | 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 thionyl chloride Heating; | 95% |
With thionyl chloride 1.) r. t., 1 h, 2.) reflux, 0.5 h; | 87% |
With thionyl chloride 1) room temperature, 1 h; 2) reflux, 0.5 h; | 87% |
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane at 0 - 20℃; for 6h; | 92% |
With N-ethyl-N,N-diisopropylamine In acetonitrile at 10 - 20℃; for 72h; |
Conditions | Yield |
---|---|
With thionyl chloride In ethanol 1) 0 deg C; 2) 1 h, room temp., then 0.5 h reflux; | 84% |
With thionyl chloride In ethanol; water | |
Multi-step reaction with 2 steps 1: 0.83 h / 220 - 290 °C / Autoclave; Large scale 2: toluene-4-sulfonic acid / methanol / -5 - 45 °C View Scheme |
ethanol
(S)-5-oxopyrrolidine-2-carbonyl chloride
ethyl (S)-pyroglutamate
Conditions | Yield |
---|---|
In dichloromethane for 0.0833333h; Heating; | 81% |
L-glutamic acid diethyl ester
ethyl (S)-pyroglutamate
Conditions | Yield |
---|---|
at 150℃; under 15.0015 Torr; Inert atmosphere; |
di-tert-butyl dicarbonate
ethyl (S)-pyroglutamate
(S)-ethyl N-tert-butoxycarbonylpyroglutamate
Conditions | Yield |
---|---|
With dmap In acetonitrile at 20℃; | 100% |
With dmap In dichloromethane at 20℃; for 6h; | 100% |
With dmap In acetonitrile at 20℃; for 3h; | 98% |
2-bromobenzaldehyde O-(phenylmethyl)oxime
ethyl (S)-pyroglutamate
(S)-1-[2-(Benzyloxyimino-methyl)-phenyl]-5-oxo-pyrrolidine-2-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 100℃; | 99% |
2-bromobenzaldehyde O-(phenylmethyl)oxime
ethyl (S)-pyroglutamate
(S)-5-oxo-1-[2-[(E)-(phenylmethoxyimino)methyl]phenyl]proline ethyl ester
Conditions | Yield |
---|---|
With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 100℃; for 8h; | 99% |
methyl 4-bromo-3-[(phenylmethoxyimino)methyl]benzoate
ethyl (S)-pyroglutamate
(S)-1-[2-(Benzyloxyimino-methyl)-4-methoxycarbonyl-phenyl]-5-oxo-pyrrolidine-2-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 100℃; | 98% |
methyl 4-bromo-3-[(phenylmethoxyimino)methyl]benzoate
ethyl (S)-pyroglutamate
(S)-1-[4-(methoxycarbonyl)-2-[(E)-(phenylmethoxyimino)methyl]phenyl]-5-oxoproline ethyl ester
Conditions | Yield |
---|---|
With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 100℃; for 8h; | 98% |
triethyloxonium fluoroborate
ethyl (S)-pyroglutamate
ethyl (2S)-5-ethoxy-3,4-dihydro-2H-pyrrole-2-carboxylate
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 20℃; for 12h; regioselective reaction; | 97% |
92% | |
In dichloromethane at 20℃; for 40h; | 92% |
In chloroform at 5℃; for 4h; | 69% |
In dichloromethane at 20℃; for 168h; | 56% |
ethyl bromoacetate
ethyl (S)-pyroglutamate
L-1-<(Ethoxycarbonyl)methyl>-5-oxoprolin-ethylester
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran; paraffin at 0℃; 20-30 min; | 97% |
With sodium hydride 1.) benzene, r.t., 30 min; 50-60 deg C, 10 min, 2.) r.t., 2 h; Yield given. Multistep reaction; |
ethyl (S)-pyroglutamate
(S)-Pyroglutaminol
Conditions | Yield |
---|---|
With potassium borohydride; lithium chloride In tetrahydrofuran at -15 - 20℃; for 2h; Reagent/catalyst; | 95% |
With lithium borohydride In tetrahydrofuran at 20℃; for 48h; | 90% |
With sodium tetrahydroborate In ethanol | 83% |
phosgene
ethyl (S)-pyroglutamate
L-1-(chlorocarbonyl)proline ethyl ester
Conditions | Yield |
---|---|
In chloroform at 5 - 40℃; for 29h; | 95% |
benzyl bromide
ethyl (S)-pyroglutamate
(S)-(+)-1-(benzyl)-5-oxopyrrolidine-2-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran; paraffin at 0℃; 20-30 min; | 95% |
With sodium hydride 1) THF, mineral oil, 0.25 h, 2) THF, mineral oil, room temperature, 2 h; Yield given. Multistep reaction; | |
With potassium tert-butylate In tetrahydrofuran; water; ethyl acetate | |
With tert-BuOK In tetrahydrofuran; water; ethyl acetate | |
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 24.5h; |
methyl chloroformate
ethyl (S)-pyroglutamate
ethyl N-methoxycarbonyl-L-pyroglutamate
Conditions | Yield |
---|---|
With dmap; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 8h; | 95% |
allyl bromide
ethyl (S)-pyroglutamate
(S)-1-allyl-5-oxo-pyrrolidine-2-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran; paraffin at 0℃; 20-30 min; | 94% |
With potassium hydroxide; tetrabutylammomium bromide In tetrahydrofuran sonication (ultrasonic cleaning bath); | 81% |
With sodium hydride In tetrahydrofuran at 20℃; | 80% |
With potassium hydroxide; tetra-(n-butyl)ammonium iodide In tetrahydrofuran Ambient temperature; sonic bath; | 78% |
With potassium hydroxide; tetra-(n-butyl)ammonium iodide In tetrahydrofuran Ambient temperature; sonication; | 43% |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran; paraffin at 0℃; 20-30 min; | 93% |
carbon monoxide
2-(2-iodophenyl)acetonitrile
ethyl (S)-pyroglutamate
(S)-ethyl 10-cyano-5-oxo-1,2,3,5-tetrahydropyrrolo[1,2-b]isoquinoline-3-carboxylate
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate; triphenylphosphine In tetrahydrofuran at 80℃; under 10343.2 Torr; for 24h; Autoclave; | 93% |
ethyl (S)-pyroglutamate
ethyl (2S)-5-thioxo-3,4-dihydro-5H-pyrrole-2-carboxylate
Conditions | Yield |
---|---|
With Lawessons reagent In toluene for 1h; Heating; | 92% |
With Lawessons reagent In tetrahydrofuran Ambient temperature; | 90% |
With Lawessons reagent In tetrahydrofuran at 20℃; for 1h; | 90% |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran; paraffin at 0℃; 20-30 min; | 92% |
With sodium hydride Yield given. Multistep reaction; | |
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; | |
Stage #1: ethyl (S)-pyroglutamate With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.25h; Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 20℃; for 96h; |
carbon monoxide
ethyl 2-(2-iodophenyl)acetate
ethyl (S)-pyroglutamate
(S)-diethyl 5-oxo-1,2,3,5-tetrahydropyrrolo[1,2-b]isoquinoline-3,10-dicarboxylate
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate; triphenylphosphine In tetrahydrofuran at 80℃; under 10343.2 Torr; for 24h; Autoclave; | 92% |
2-carbomethoxyaniline
ethyl (S)-pyroglutamate
9-oxo-1,2,3,9-tetrahydro-pyrrolo[2,1-b]quinazoline-1-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With trichlorophosphate In 1,2-dichloro-ethane for 3h; Heating; | 91% |
carbon monoxide
ethyl (S)-pyroglutamate
(S)-diethyl 5-oxo-5,7,8,9-tetrahydro-[1,3]dioxolo[4,5-g]pyrrolo[1,2-b]isoquinoline-7,10-dicarboxylate
Conditions | Yield |
---|---|
With palladium diacetate; caesium carbonate; triphenylphosphine In tetrahydrofuran at 80℃; under 10343.2 Torr; for 24h; Autoclave; | 90% |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 20℃; | 89% |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 20℃; for 16h; | 89% |
Conditions | Yield |
---|---|
With sodium hydride In diethyl ether at 20℃; for 1h; | 89% |
chloroformic acid ethyl ester
ethyl (S)-pyroglutamate
ethyl (S)-N-(ethoxycarbonyl)pyroglutamate
Conditions | Yield |
---|---|
With dmap; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 8h; | 88% |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 20℃; | 87% |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 20℃; for 16h; | 87% |
(fluorenylmethoxy)carbonyl chloride
ethyl (S)-pyroglutamate
Conditions | Yield |
---|---|
Stage #1: ethyl (S)-pyroglutamate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.333333h; Inert atmosphere; Stage #2: (fluorenylmethoxy)carbonyl chloride In tetrahydrofuran at -78 - 20℃; for 20h; Inert atmosphere; | 87% |
Stage #1: ethyl (S)-pyroglutamate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: (fluorenylmethoxy)carbonyl chloride In tetrahydrofuran at -78 - 20℃; for 20h; Inert atmosphere; | 87% |
Stage #1: ethyl (S)-pyroglutamate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.25h; Inert atmosphere; Stage #2: (fluorenylmethoxy)carbonyl chloride In tetrahydrofuran at -78 - 20℃; for 16h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water | 83% |
Molecular Formula: C7H11NO3
Molar mass: 157.178 g/mol
EINECS: 230-480-9
Density: 1.161 g/cm3
Flash Point: 142.9 °C
Index of Refraction: 1.466
Boiling Point: 312.7 °C at 760 mmHg
Vapour Pressure: 0.000519 mmHg at 25°C
Melting point: 54-56 °C
Storage temp: 0-6°C
Appearance: White to cream low melting solid
Product categories: pharmacetical;Pyroglutamic acid [Pyr, pGu];Chiral and Miscellaneous Reagents;Heterocycles
Structure of Ethyl L-pyroglutamate (7149-65-7):
XLogP3-AA: -0.1
H-Bond Donor: 1
H-Bond Acceptor: 3
Systematic Name: Ethyl (2S)-5-oxopyrrolidine-2-carboxylate
SMILES: O=C(OCC)[C@H]1NC(=O)CC1
InChI: InChI=1/C7H11NO3/c1-2-11-7(10)5-3-4-6(9)8-5/h5H,2-4H2,1H3,(H,8,9)/t5-/m0/s1
InChIKey: QYJOOVQLTTVTJY-YFKPBYRVBB
Std. InChI: InChI=1S/C7H11NO3/c1-2-11-7(10)5-3-4-6(9)8-5/h5H,2-4H2,1H3,(H,8,9)/t5-/m0/s1
Std. InChIKey: QYJOOVQLTTVTJY-YFKPBYRVSA-N
Carcinogenicity of Ethyl L-pyroglutamate (7149-65-7) hasn't been listed as a carcinogen by NTP, IARC,ACGIH, or CA Prop 65. And its toxicological properties have not been fully investigated.
Hazard Codes: Xi
Risk Statements:
36: Irritating to the eyes
37: Irritating to the respiratory system
38: Irritating to the skin
Safety Statements:
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
37: Wear suitable gloves
39: Wear eye/face protection
Ethyl L-pyroglutamate (7149-65-7) also can be called (S)-5-Oxoproline ethyl ester ; Ethyl (S)-(+)-2-pyrrolidone-5-carboxylate ; Ethyl 5-oxo-2-pyrrolidinecarboxylate ; Aclaplastin ;L-Pyroglutamic acid ethyl ester.It is hazardous,so the first aid measures and others should be known.Such as: When on the skin: first,should flush skin with plenty of water immediatelyfor at least 15 minutes while removing contaminated clothing. Secondly,Get shoesmedical aid . Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids.Then get medical aid soon.While ,it's Inhaled: Remove from exposure and move to fresh air immediately.Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product : Wash mouth out with water,and get medical aid immediately.Notes to physician: Treat supportively and symptomatically.
In addition, Ethyl L-pyroglutamate (7149-65-7) is not compatible with strong oxidizing agents,strong bases, and you must not take it with incompatible materials.And also prevent it to broken down into hazardous decomposition products: oxides of nitrogen,carbon dioxide,carbon monoxide.
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