(S)-2-Hydroxy-2-(6-(hydroxymethyl)-5-oxo-2,3-dihydro-5H-spiro[indolizine-1,2'-[1,3]dioxolan]-7-yl)-N-((S)-1-phenylethyl)butanamide → (4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano(3,4-f)indolizine-3,6,10(4H)-trione

HRID 868315ノート

反応式

HRID 868315 の反応式
[CH2:1]([C@:3]([OH:31])([C:15]1[CH:23]=[C:22]2[N:18]([CH2:19][CH2:20][C:21]32OCC[O:24]3)[C:17](=[O:28])[C:16]=1[CH2:29][OH:30])[C:4](N[C@H](C1C=CC=CC=1)C)=[O:5])[CH3:2]>FC(F)(F)C(O)=O>[CH2:1]([C@:3]1([OH:31])[C:15]2[CH:23]=[C:22]3[N:18]([CH2:19][CH2:20][C:21]3=[O:24])[C:17](=[O:28])[C:16]=2[CH2:29][O:30][C:4]1=[O:5])[CH3:2]

参加物

3

反応物 1

HCID 11122829(S)-2-Hydroxy-2-(6-(hydroxymethyl)-5-oxo-2,3-dihydro-5H-spiro[indolizine-1,2'-[1,3]dioxolan]-7-yl)-N-((S)-1-phenylethyl)butanamide

生成物 1

HCID 10220900(4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano(3,4-f)indolizine-3,6,10(4H)-trione収率 92.2%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

Three hundred milligrams of the compound (VII) obtained in the above procedure (1) were dissolved in 80% trifluoroacetic acid solution and the resulting mixture was stirred at room temperature for 2 hours under a nitrogen gas stream. The reaction mixture was concentrated to dryness and the residue was purified by column chromatography on silica gel (10 g). A colorless oily substance was obtained from a 98:2 eluate of chloroform and methanol. The oily substance was crystallized from a mixed solvent of ethanol and petroleum ether to obtain 170 mg of the title compound as colorless needle-like crystals.

後処理

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe residue was purified by column chromatography on silica gel (10 g)
  3. customA colorless oily substance was obtained from a 98:2 eluate of chloroform and methanol
  4. customThe oily substance was crystallized from a mixed solvent of ethanol and petroleum ether

出典と根拠

ORDレコード
ord-af3463de5c3049afa97c6e8c001aff25
出典データセット
uspto-grants-1988_10
特許番号
US04778891

反応ノート

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