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Home > Encyclopedia > 1-(1,1-Dimethylethyl) 2-(phenylmethyl) (2S)-5-oxo-1,2-pyrrolidinedicarboxylate

1-(1,1-Dimethylethyl) 2-(phenylmethyl) (2S)-5-oxo-1,2-pyrrolidinedicarboxylate

1-(1,1-Dimethylethyl) 2-(phenylmethyl) (2S)-5-oxo-1,2-pyrrolidinedicarboxylate structure

1-(1,1-Dimethylethyl) 2-(phenylmethyl) (2S)-5-oxo-1,2-pyrrolidinedicarboxylate 

structure
  • CAS No:

    113400-36-5

  • Formula:

    C17H21NO5

  • Chemical Name:

    1-(1,1-Dimethylethyl) 2-(phenylmethyl) (2S)-5-oxo-1,2-pyrrolidinedicarboxylate

  • Synonyms:

    1,2-Pyrrolidinedicarboxylic acid,5-oxo-,1-(1,1-dimethylethyl) 2-(phenylmethyl) ester,(2S)-;1,2-Pyrrolidinedicarboxylic acid,5-oxo-,1-(1,1-dimethylethyl) 2-(phenylmethyl) ester,(S)-;1-(1,1-Dimethylethyl) 2-(phenylmethyl) (2S)-5-oxo-1,2-pyrrolidinedicarboxylate;2-Benzyl 1-tert-butyl (2S)-5-oxopyrrolidine-1,2-dicarboxylate;Benzyl N-Boc-pyroglutamate;N-tert-Butoxycarbonylpyroglutamic acid benzyl ester;(S)-2-Benzyl 1-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate;2-Benzyl 1-(tert-butyl) (S)-5-oxopyrrolidine-1,2-dicarboxylate;2-Benzyl 1-tert-butyl (2S)-5-oxopyrrolidine-1,2-dicarboxylate

  • Categories:

    Biochemical Engineering  >  Amino Acids and Derivatives

1-(1,1-Dimethylethyl) 2-(phenylmethyl) (2S)-5-oxo-1,2-pyrrolidinedicarboxylate Basic Attributes

319

319.35

601-251-4

2933790090

Characteristics

72.9

2.4

1.219

69-70 °C

464.9±38.0 °C(Predicted)

235.0±26.8 °C

1.542

1-(1,1-Dimethylethyl) 2-(phenylmethyl) (2S)-5-oxo-1,2-pyrrolidinedicarboxylate Use and Manufacturing

D-1 (8 g, 36.5 mmol, 1 eq) was dissolved in DCM (150 mL). The mixture was stirred and was cooled to 0° C. Dimethylaminopyridine (DMAP, 4.9 g, 40.1 mmol, 1.1 eq) was added followed by Boc-anhydride ((BOC)Benzyl chloride (25.3ml, 0.22mol) was added to a solution of 5-oxo-l-proline (2) (25.8g, 0.20mol) with triethylamine (28.0ml, 0.20mol) in THF (260ml). The reaction mixture was refluxed at 70°C for 5days. After cooling the mixture to room temperature, the solvent was removed in vacuo. The residue was diluted with water, and extracted with chloroform. The organic layer was washed with brine, and dried over magnesium sulfate. The mixture was filtered, and the solvent was removed in vacuo to afford the crude product as pale brown oil. To a stirred solution of the product in dichloromethane (400ml) was added di-tert-butyl dicarbonate (44g, 0.20mol), triethylamine (28ml, 0.2mol) and DMAP (12.2g, 0.10mol) under an ice cooling bath. The solution was warmed to room temperature and stirred for 16h. The reaction mixture was diluted with water, and extracted with chloroform. The organic layer was washed with brine, and dried over magnesium sulfate. The mixture was filtered, and the solvent was removed in vacuo to afford crude product. The residue was purified by flash silica gel chromatography withn-hexane/EtOAc (2:1, v/v) to give the colorless solid (51.2g, 80percent yield);To a 500 ml four-necked flask equipped with a stirrer, a thermometer and a reflux condenser was added 18.2 g (0.05 mol) of L-glutamic acid dibenzyl ester hydrochloride prepared in Example 1, 150 g of toluene, 7.8 g (0.06 mol) of diisopropylethylamine, 12.0 g (0.055 mol) di-tert-butyl dicarbonate, heated, 30-35°C for 4 hours, 90-95°C for 5 hours, Cool to 2025°C, filter and distill the filtrate to recover the solvent.To the residue was added 50 g of methyl tert-butyl ether, recrystallized, filtered and dried.15.1 g of white powder solidN-tert-butyloxycarbonyl-L-pyroglutamic acid benzyl esterThe liquid phase purity was 99.9percent and the yield was 94.6percent.

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