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Triphenylphosphine → HCID 58505712, 화합물

HRID 1917602
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HRID 1917602 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[N:18]3[C:13]([CH:14]=[C:15]([OH:19])[CH:16]=[CH:17]3)=[C:12]([C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[C:11]=2[CH2:26][C:27]([CH3:34])([CH3:33])[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:9])=[CH:4][CH:3]=1.[CH3:35][O:36][C:37]1[N:42]=[C:41]([CH2:43]O)[CH:40]=[CH:39][CH:38]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[N:18]3[C:13]([CH:14]=[C:15]([O:19][CH2:43][C:41]4[CH:40]=[CH:39][CH:38]=[C:37]([O:36][CH3:35])[N:42]=4)[CH:16]=[CH:17]3)=[C:12]([C:20](=[O:25])[C:21]([CH3:23])([CH3:24])[CH3:22])[C:11]=2[CH2:26][C:27]([CH3:33])([CH3:34])[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:9])=[CH:6][CH:7]=1
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6

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HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 12325389(6-Methoxypyridin-2-yl)methanolHCID 178471307HCID 178471307, 화합물

생성물 1

HCID 58505712HCID 58505712, 화합물수율 16%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
23 °C

실험 절차

To a cold (0° C.) solution of ethyl 3-{3-[(4-chlorophenyl)carbonyl]-1-(2,2-dimethylpropanoyl)-7-hydroxyindolizin-2-yl}-2,2-dimethylpropanoate (100 mg, 0.21 mmol), (6-methoxy-pyridin-2-yl)-methanol (35 mg, 0.25 mmol), and triphenylphosphine (65 mg, 0.25 mmol) in THF (5 mL) is added DIAD (48 μL, 0.25 mmol). The reaction is allowed to gradually warm to 23° C. and then stirred overnight. Silica gel is added and the mixture is concentrated in vacuo then purified by flash chromatography (SiO2, hexanes to 15% EtOAc in hexanes) to give ethyl 3-{3-[(4-chlorophenyl)carbonyl]-1-(2,2-dimethylpropanoyl)-7-[(6-methoxypyridin-2-yl)methoxy]indolizin-2-yl}-2,2-dimethylpropanoate (20 mg, 16%).

후처리

  1. additionSilica gel is added
  2. concentrationthe mixture is concentrated in vacuo
  3. customthen purified by flash chromatography (SiO2, hexanes to 15% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-0dfff31ea4be4c95b9d3fb11e5b6018d
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08618300B2

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