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

HRID 1608972ノート

反応式

HRID 1608972 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d9b211ccbf36478eb6738b4ed66f9abb
出典データセット
uspto-grants-1995_03
特許番号
US05399574

反応ノート

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