ChemicalBook CAS DataBase List H-Glu(OMe)-OtBu

H-Glu(OMe)-OtBu synthesis

13synthesis methods

Product Name:H-Glu(OMe)-OtBu
CAS Number:79640-72-5
Molecular formula:C10H19NO4
Molecular Weight:217.26

540-88-5

5-methyl L-2-aminoglutarate hydrochloride

3077-51-8

79640-72-5

GENERAL METHOD: Under vigorous stirring conditions, 82 mL of tert-butyl acetate was slowly added to 2.45 mL of 58% HClO4 solution containing 12.2 mmol of methyl ester 6 or 7 hydrochloride. The reaction mixture was stirred continuously at room temperature for 72 hours. Upon completion of the reaction, the mixture was slowly poured into a mixture of 270 mL of 10% Na2CO3 solution with 40 mL of Et2O that had been pre-cooled to 5°C. After separation of the organic phase, the aqueous phase was extracted with Et2O (2 x 70 mL) to recover the reaction product. All organic phases were combined and washed sequentially with 10% Na2CO3 solution (2 × 100 mL), dried over anhydrous Na2SO4 and subsequently concentrated under reduced pressure. The crude product was purified by fast column chromatography with the eluent CH2Cl2-MeOH (98:2, v/v).

540-88-5
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3077-51-8
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79640-72-5
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$55.00/500 mg

Yield: 51%

Reaction Conditions:

with perchloric acid at 20; for 72 h;

Steps:

Diesters 8 and 9. General procedure
General procedure: tert-Butylacetate (82 mL) was added to a solution of hydrochloride of methyl ester 6 or 7 (12.2 mmol) in 2.45 mL of 58 % HClO₄ at vigorous stirring. The mixture was stirred at room temperature for 72 h, then poured into cooled (5 °C) mixture of 270 mL of 10 %Na₂CO₃ solution and 40 mL of Et₂O. The organic layer was separated, the reaction products were extracted from the aqueous layer with Et₂O (2 × 70 mL). Combined organic layers were washed with 10 %solution of Na₂CO₃ (2 × 100 mL), dried over Na₂SO₄, and evaporated. The residue was purified by flashch romatography (eluent CH₂Cl₂-MeOH, 98 : 2).

References:

Gruzdev;Levit;Olshevskaya;Krasnov [Russian Journal of Organic Chemistry,2017,vol. 53,# 5,p. 769 - 776][Zh. Org. Khim.,2017,vol. 53,# 5,p. 756 - 762,7]

57732-63-5 Synthesis