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205524-46-5

205524-46-5 Structure

205524-46-5 Structure
IdentificationBack Directory
[Name]

D-PYROGLUTAMIC ACID TERT-BUTYL ESTER
[CAS]

205524-46-5
[Synonyms]

idone-5-carboxyL
tert-butyl 5-oxo-D-prolinate
5-Oxo-D-proline tert-butyl ester
D-PyroglutaMic acid ter-butyl ester
D-PYROGLUTAMIC ACID TERT-BUTYL ESTER
2-Methyl-2-propanyl 5-oxo-D-prolinate
5-oxo-D-Proline1,1-dimethylethyl ester
D-Proline, 5-oxo-, 1,1-dimethylethyl ester
tert-Butyl (R)-2-Pyrrolidone-5-carboxylate
ert-butyl(2R)-5-oxopyrrolidine-2-carboxylate
(R)-tert-Butyl 5-oxopyrrolidine-2-carboxylate
tert-butyl (2R)-5-oxopyrrolidine-2-carboxylate
D-PYROGLUTAMIC ACID TERT-BUTYL ESTER USP/EP/BP
(R)-5-Oxo-pyrrolidine-2-carboxylic acid tert-butyl ester
[Molecular Formula]

C9H15NO3
[MDL Number]

MFCD09261417
[MOL File]

205524-46-5.mol
[Molecular Weight]

185.22
Chemical PropertiesBack Directory
[Boiling point ]

319℃
[density ]

1.099
[Fp ]

147℃
[storage temp. ]

2-8°C
[pka]

14.65±0.40(Predicted)
[Appearance]

White to off-white Solid
[Optical Rotation]

Consistent with structure
[InChI]

InChI=1S/C9H15NO3/c1-9(2,3)13-8(12)6-4-5-7(11)10-6/h6H,4-5H2,1-3H3,(H,10,11)/t6-/m1/s1
[InChIKey]

QXGSPAGZWRTTOT-ZCFIWIBFSA-N
[SMILES]

C(OC(C)(C)C)(=O)[C@H]1CCC(=O)N1
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P280-P301+P312-P302+P352-P305+P351+P338
[HS Code ]

2933790090
Spectrum DetailBack Directory
[Spectrum Detail]

D-PYROGLUTAMIC ACID TERT-BUTYL ESTER (205524-46-5)1HNMR
Hazard InformationBack Directory
[Synthesis]

tert-Butyl acetate

540-88-5

D-Pyroglutamic acid

4042-36-8

D-PYROGLUTAMIC ACID TERT-BUTYL ESTER

205524-46-5

The general procedure for the synthesis of tert-butyl D-pyroglutamate from tert-butyl acetate and D-(+)-pyroglutamic acid was as follows: (R)-5-oxopyrrolidine-2-carboxylic acid (3.21 g, 24.9 mmol) was dissolved in tert-butyl acetate (100 mL) under argon protection. Subsequently, 60% aqueous perchloric acid (1.5 mL) was slowly added at room temperature. The reaction mixture was stirred at room temperature for 24 hours in an argon atmosphere. Upon completion of the reaction, saturated aqueous sodium bicarbonate solution (50 mL) was added to the mixture to neutralize the reaction solution, followed by extraction with chloroform (3 x 30 mL). The organic layers were combined, dried with anhydrous sodium sulfate, filtered and the solvent was removed by distillation under reduced pressure to afford tert-butyl (R)-5-oxopyrrolidine-2-carboxylate (4.62 g, yield) as a white solid. The physical properties of the product are described below.

[References]

[1] Chemistry - A European Journal, 2016, vol. 22, # 27, p. 9330 - 9337
[2] Patent: JP6095208, 2017, B2. Location in patent: Paragraph 0036-0038
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