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Phosphorus sulfide (P2S5) → 6-chloro-4'-[5-chloro-2-(1-ethoxycarbonyl-1-propyl-butoxy)-phenyl]-2'-(5-fluoro-2-methyl-phenyl)-6'-thioxo spiro[3H-indole-3,3'-piperidine]-2(1H)-one

HRID 658931
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HRID 658931 반응식
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:45])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][C:24]([C:31]([O:33][CH2:34][CH3:35])=[O:32])([CH2:28][CH2:29][CH3:30])[CH2:25][CH2:26][CH3:27])[CH2:14][C:13](=O)[NH:12][CH:11]3[C:37]3[CH:42]=[C:41]([F:43])[CH:40]=[CH:39][C:38]=3[CH3:44])[C:5]2=[CH:4][CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:47]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:45])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][C:24]([C:31]([O:33][CH2:34][CH3:35])=[O:32])([CH2:28][CH2:29][CH3:30])[CH2:25][CH2:26][CH3:27])[CH2:14][C:13](=[S:47])[NH:12][CH:11]3[C:37]3[CH:42]=[C:41]([F:43])[CH:40]=[CH:39][C:38]=3[CH3:44])[C:5]2=[CH:4][CH:3]=1
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참가 물질

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HCID 14817Phosphorus sulfide (P2S5)HCID 671438524'-[5-chloro-2-(1-ethoxycarbonyl-1-propyl-butoxy)-phenyl]-6-chloro-2'-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

생성물 1

HCID 752934056-chloro-4'-[5-chloro-2-(1-ethoxycarbonyl-1-propyl-butoxy)-phenyl]-2'-(5-fluoro-2-methyl-phenyl)-6'-thioxo spiro[3H-indole-3,3'-piperidine]-2(1H)-one수율 64.5%

시약·촉매·용매 1

HCID 1140
Toluene
용매

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온도
60 °C

실험 절차

A mixture of racemic (2′S, 3S, 4′R)-6-chloro-4′-[5-chloro-2-(1-ethoxycarbonyl-1-propyl-butoxy)-phenyl]-2′-(5-fluoro-2-methyl-phenyl) spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (100 mg, 0.15 mmol) and P2S5 (70 mg, 0.31 mmol) was heated at 60° C. for 2 h, and then diluted with toluene (10 mL). The mixture was concentrated in vacuo and the residue was washed with DCM for 2 times. The DCM solution was combined and concentrated. The residue was purified by flash column to give the title compound as white solid (65 mg).

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. washthe residue was washed with DCM for 2 times
  3. concentrationconcentrated
  4. customThe residue was purified by flash column

출처 및 근거

ORD 기록
ord-f04e25d0b3544c9faaabb5d9a38be11b
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08076482B2

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