Phosgene → (S)-4-(4-Nitrobenzyl)oxazolidin-2-one

HRID 1608972노트

반응식

HRID 1608972 반응식
[NH2:1][C@@H:2]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)[CH2:3][OH:4].[OH-].[K+].[C:17](Cl)(Cl)=[O:18]>C1(C)C=CC=CC=1.O>[N+:12]([C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C@H:2]2[CH2:3][O:4][C:17](=[O:18])[NH:1]2)=[CH:7][CH:8]=1)([O-:14])=[O:13]

참가 물질

6

반응물 3

HCID 6371PhosgeneHCID 14797Potassium HydroxideHCID 10397777(S)-2-Amino-3-(4-nitrophenyl)propan-1-ol

생성물 1

HCID 10353477(S)-4-(4-Nitrobenzyl)oxazolidin-2-one

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매2회

반응 조건

온도
0 °C

실험 절차

The product from step (b) (4.9 g) was suspended in toluene, the suspension cooled to 0° C. and a solution of potassium hydroxide (7.0 g) in water (56 ml) added dropwise. A solution of phosgene (62.5 ml of a 12% w/v solution in toluene) was added dropwise to the resulting solution over 30 minutes and stirring continued for 1 hour. The mixture was extracted with ethyl acetate and the extracts washed with brine, dried and evaporated in vacuo to give a yellow oil. Crystallisation from ethyl acetate gave the desired product as pale yellow crystals (2.3 g).

후처리

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe extracts washed with brine
  3. customdried
  4. customevaporated in vacuo
  5. customto give a yellow oil
  6. customCrystallisation from ethyl acetate

출처 및 근거

ORD 기록
ord-d9b211ccbf36478eb6738b4ed66f9abb
출처 데이터셋
uspto-grants-1995_03
특허 번호
US05399574

반응 노트

불러오는 중…