반응 #439519

반응 방정식

(S)-2-amino-4-butyrolactone hydrobromide

diisopropylethylamine

N1-phenyl-1,2-benzenediamine

diisopropylethylamine

triphosgene

→

N-(2-anilinophenyl)-N′-[(3S)-2-oxotetrahydro-3-furanyl]urea

용매

CH2Cl2

CH2Cl2

CH2Cl2

반응 조건

후처리

1. 1
   농축After concentration to dryness under vacuum
2. 2
   workup.STIRRINGAfter stirring
3. 3
   기타decanting
4. 4
   세척the organic phase is washed successively with 50 ml of water and 50 ml of salt water
5. 5
   건조The organic solution is then dried over Na2SO4
6. 6
   여과filtered
7. 7
   농축concentrated under vacuum
8. 8
   기타The evaporation residue is then purified on a silica column (eluent: Heptane/AcOEt: 1/2)

실험 절차

A solution of 1.48 g (8.15 mmoles) of (S)-2-amino-4-butyrolactone hydrobromide and 3.12 ml (17.9 mmoles) of diisopropylethylamine in 80 ml of anhydrous CH2Cl2 is added slowly (4 hours) into a three-necked flask containing a solution of 0.89 g (3 mmoles) of triphosgene in 45 ml of anhydrous CH2Cl2, under an inert atmosphere. After stirring for a further 15 minutes, a solution of 1.5 g (8.15 mmoles) of N1-phenyl-1,2-benzenediamine and 3.12 ml (17.9 mmoles) of diisopropylethylamine in 45 ml of anhydrous CH2Cl2 is added in one go. The reaction mixture is then heated for 5 hours at 60° C. After concentration to dryness under vacuum, the residue is divided between 50 ml of AcOEt and 50 ml of water. After stirring and decanting, the organic phase is washed successively with 50 ml of water and 50 ml of salt water. The organic solution is then dried over Na2SO4, filtered and concentrated under vacuum. The evaporation residue is then purified on a silica column (eluent: Heptane/AcOEt: 1/2). Pink solid.

출처