Triphenylphosphine → (4S)-4-acetylthio-2-pyrrolidone

HRID 248209ノート

反応式

HRID 248209 の反応式
[OH:1][C@H:2]1[CH2:6][NH:5][C:4](=O)[CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[C:39](O)(=[S:41])[CH3:40]>O1CCCC1>[C:2]([C@@H:3]1[CH2:4][NH:5][C:39](=[S:41])[CH2:40]1)(=[O:1])[CH3:6]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 185505(R)-(+)-4-Hydroxy-2-pyrrolidinoneHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178418634HCID 178418634、化合物

生成物 1

HCID 86746170(4S)-4-acetylthio-2-pyrrolidone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(4R)-4-Hydroxy-2-pyrrolidone (4.5 g) is suspended in tetrahydrofuran (300 ml), and thereto is added triphenylphosphine (23.4 g). After stirring the mixture for 10 minutes, diethyl azodicarboxylate (14 ml) is added dropwise to the mixture below -10° C., and the mixture is stirred at the same temperature for 10 minutes. Thioacetic acid (6.3 ml) is added dropwise to the reaction mixture below -10° C., and the mixture is stirred at the same temperature for 2 hours, and the solvent is evaporated under reduced pressure. The residue is crystallized from diisopropyl ether, and the precipitate is removed by filtration. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (eluent, chloroform : ethanol =98:2) to give (4S)-4-acetylthio-2-pyrrolidone (3.8 g) as an oil.

後処理

  1. stirringthe mixture is stirred at the same temperature for 10 minutes
  2. stirringthe mixture is stirred at the same temperature for 2 hours
  3. customthe solvent is evaporated under reduced pressure
  4. customThe residue is crystallized from diisopropyl ether
  5. customthe precipitate is removed by filtration
  6. concentrationThe filtrate is concentrated under reduced pressure
  7. customthe residue is purified by silica gel column chromatography (eluent, chloroform : ethanol =98:2)

出典と根拠

ORDレコード
ord-f5ade569c9b14b48a955d4914a3cf2a0
出典データセット
uspto-grants-1993_05
特許番号
US05208348

反応ノート

読み込み中…