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Chemical Structure| 4931-66-2 Chemical Structure| 4931-66-2
Chemical Structure| 4931-66-2

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H-Pyr-OMe (L-Pyroglutamic acid methyl ester) is isolated from cabbage and exhibits anti-inflammatory activity.

Synonyms: (S)-Methyl 5-oxopyrrolidine-2-carboxylate; L-Pyroglutamic acid methyl ester; Methyl L-pyroglutamate

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Product Details of H-Pyr-OMe

CAS No. :4931-66-2
Formula : C6H9NO3
M.W : 143.14
SMILES Code : O=C1N[C@H](C(OC)=O)CC1
Synonyms :
(S)-Methyl 5-oxopyrrolidine-2-carboxylate; L-Pyroglutamic acid methyl ester; Methyl L-pyroglutamate
MDL No. :MFCD00080931
InChI Key :HQGPKMSGXAUKHT-BYPYZUCNSA-N
Pubchem ID :78646

Safety of H-Pyr-OMe

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of H-Pyr-OMe

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 4931-66-2 ]

[ 4931-66-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 1700-31-8 ]
  • [ 4931-66-2 ]
  • [ 1308718-80-0 ]
YieldReaction ConditionsOperation in experiment
65% With sodium hydride; In tetrahydrofuran; paraffin oil; at 0 - 20℃; General procedure: Methyl (S)-pyrroglutamate (2) or O-protected-S-pyrroglutaminol (9a, b) (1 mmoL) was dissolved in dry THF (3 mL), followed by the addition of the appropriate benzyl bromide (1.1 mmoL). The reaction mixture was cooled at 0 °C and NaH (60percent in paraffin oil, 60 mg) was added in portions. The stirring was continued for 30 min at 0 °C and 2-4 h at rt. The reaction was quenched by the addition of saturated solution of NH4Cl, the organic solvent was evaporated and the residue was dissolved in ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and evaporated under reduced pressure. The product was purified by column chromatography (Silica Gel 60) using the appropriate solvent systems as it will be defined in each case below.
  • 2
  • [ 67107-87-3 ]
  • [ 4931-66-2 ]
  • C17H34N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% In 1,4-dioxane; at 75℃; for 4h; Example 14A reaction vessel was charged with 260 parts by weight of <strong>[67107-87-3]12-amino-1-dodecanol</strong>, 184 parts by weight of methyl L-pyroglutamate, and 120 parts by weight of 1,4-dioxane, and the mixture was stirred at 75 C. for 4 hours. The resulting reaction mixture was stripped at 110 C. under reduced pressure to remove the 1,4-dioxane, and 408 parts by weight of white solid was obtained at a yield of 92%. Results of the 13C-NMR shown in Table 14, below, and absorption at 1685 cm-1 (from amide bond) in the measurement of IR spectrum confirmed that the resulting product was an amino acid compound represented by the following formula: TABLE 14 13C-NMR (CDCl3) 64.6ppm (-CH2-OH) 22~31.9ppm (-(CH2)10-] 39.6ppm (-CH2-NH-) 178.4ppm (-NH-CO-) 25.2ppm (-CO-CH2-CH2-) 28.6ppm (-CO-CH2-CH2-) 58.9ppm [-CH(NH2)(COOCH3)] 174.8ppm (-COOCH3) 59.3ppm (-COOCH3)
  • 3
  • [ 4931-66-2 ]
  • [ 334769-80-1 ]
 

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