(S)-4-메틸-2,5-옥사졸리딘디온

그림문자(GHS)

• 그림문자(GHS)

  

• 신호 어

  Warning

• 유해·위험 문구

  H302：삼키면 유해함

  H315：피부에 자극을 일으킴

  H319：눈에 심한 자극을 일으킴

  H332：흡입하면 유해함

  H335：호흡 자극성을 일으킬 수 있음

• 예방조치문구

  P261：분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.

  P280：보호장갑/보호의/보안경/안면보호구를 착용하시오.

  P305+P351+P338：눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.

(S)-4-메틸-2,5-옥사졸리딘디온 화학적 특성, 용도, 생산

• 용도

  (S)-4-Methyl-2,5-oxazolidonedione is composed of oxazolidine ring and 2,5-dione ring. It exhibits chirality, meaning it exists as two non-superimposable mirror image forms. Therefore, it can be used as an organic reagent for the synthesis of enantiomeric pure substances. (S)-4-Methyl-2,5-oxazolidonedione is a reagent used in the synthesis of poly(γ-benzyl-L-glutamate) and its block polypeptides with alanine, leucine and phenylalanine.

• 생산 방법

  L-alanine (20.0 g, 0.224 mol) and triphosgene (53.4 g, 0.180 mol) were suspended in 400.0 mL of dry THF bubbled with nitrogen flux in a flame-dried three-neck flask. The mixture was stirred at 60 °C for 2 h before further bubbling with nitrogen flux for 30 min. After that, the solution was precipitated in 1000.0 mL of n-hexane and stored at -20 °C. The supernatant was removed, and the residues were collected and dissolved in 200.0 mL of ethyl acetate, before two washings with 100.0mL of ice-cold water and one washing with 100.0 mL of 0.5% NaHCO3 ice-cold aqueous solution. The organic phase was then dried over anhydrous MgSO4 and evaporated to obtain 15.5 g of L-Ala NCA ((S)-4-Methyl-2,5-oxazolidonedione). The yield of L-Ala NCA was 77.5%.
  

• Synthesis Reference(s)

  The Journal of Organic Chemistry, 50, p. 2200, 1985 DOI: 10.1021/jo00212a042

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