(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 868315노트

반응식

HRID 868315 반응식
[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]

참가 물질

3

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-af3463de5c3049afa97c6e8c001aff25
출처 데이터셋
uspto-grants-1988_10
특허 번호
US04778891

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