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

HRID 36495ノート

反応式

HRID 36495 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

In 300 ml of tetrahydrofuran was suspended 4.5 g of (4R)-4-hydroxy-2-pyrrolidone, 23.4 g of triphenylphosphine was added thereto, and the mixture was stirred for 10 minutes. Subsequently, 14 ml of diethyl azodicarboxylate was added dropwise to the reaction mixture at -10° C., and the mixture was stirred at the same temperature for 10 minutes. After 6.3 ml of thioacetic acid was added drop-wise to the reaction mixture at -10° C. or lower, the mixture was stirred at the same temperature for 2 hours and the solvent was removed. The residue was crystallized from diisopropyl ether. After the crystals were removed by filtration, the filtrate was condensed under reduced pressure. The residue was purified by silica gel column chromatography (solvent; chloroform:ethanol=98:2)to obtain 3.8 g of (4S)-4-acetylthio-2-pyrrolidone as an oily product. NMR (CDCl3) δ: 2.29 (dd, 1H), 2.35 (s, 3H), 2.81 (dd, 1 H), 3.31 (dd, 1H), 3.88 (dd, 1H), 4.10 to 4.23 (m, 1H), 7.02 to 7.17 (b, 1H).

後処理

  1. additionwas added
  2. stirringthe mixture was stirred at the same temperature for 10 minutes
  3. stirringlower, the mixture was stirred at the same temperature for 2 hours
  4. customthe solvent was removed
  5. customThe residue was crystallized from diisopropyl ether
  6. customAfter the crystals were removed by filtration
  7. customcondensed under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (solvent

出典と根拠

ORDレコード
ord-7668dc4c70384c55901d6234289ad889
出典データセット
uspto-grants-1995_05
特許番号
US05414081

反応ノート

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