Tin tetrachloride → HCID 178472324、化合物

HRID 2173949ノート

反応式

HRID 2173949 の反応式
[C:1]([C:3]1[CH:51]=[CH:50][C:6]2[N:7](COCC[Si](C)(C)C)[C:8]([C:10]([C:23]3[C:31]([O:32][CH3:33])=[CH:30][C:29]([CH3:34])=[C:28]4[C:24]=3[CH:25]=[CH:26][N:27]4C(OC(C)(C)C)=O)([O:15][CH:16]([F:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:11]([F:14])([F:13])[F:12])=[N:9][C:5]=2[CH:4]=1)#[N:2].C(C1C=CC2N=C(C(C3C(OC)=CC(C)=C4C=3C=CN4C(OC(C)(C)C)=O)(OC(F)C(OCC)=O)C(F)(F)F)N(COCC[Si](C)(C)C)C=2C=1)#N.Cl[Sn](Cl)(Cl)Cl>ClCCl>[C:1]([C:3]1[CH:51]=[CH:50][C:6]2[NH:7][C:8]([C:10]([C:23]3[C:31]([O:32][CH3:33])=[CH:30][C:29]([CH3:34])=[C:28]4[C:24]=3[CH:25]=[CH:26][NH:27]4)([O:15][CH:16]([F:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:11]([F:14])([F:12])[F:13])=[N:9][C:5]=2[CH:4]=1)#[N:2]

参加物

5

反応物 3

HCID 24287Tin tetrachlorideHCID 86701509HCID 86701509、化合物HCID 86701510HCID 86701510、化合物

生成物 1

HCID 178472324HCID 178472324、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of (±)-tert-butyl 4-(1-(5-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-1-(2-ethoxy-1-fluoro-2-oxoethoxy)-2,2,2-trifluoroethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate and (±)-tert-butyl 4-(1-(6-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-1-(2-ethoxy-1-fluoro-2-oxoethoxy)-2,2,2-trifluoroethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 35-E) (94 mg, 0.128 mmol) in dichloromethane (2.0 ml) at 0° C. was added SnCl4 (1.0 M in DCM, 1.279 mL, 1.279 mmol); this mixture was stirred at 0° C. for 30 min followed by warming to room temperature and stirring for 1.0 hr additional. The reaction mixture was partitioned between EtOAc/saturated sodium bicarbonate solution upon which an emulsion formed. Both layers were filtered over a plug of Celite® and then returned to the separatory funnel as two distinct layers. The organic layer was washed with brine solution, dried over sodium sulfate, and concentrated in vacuo. The resulting residue was purified with FCC eluting with ethyl acetate/heptane (0-100%) to provide the title compound. MS (ESI+) m/z 505.2 (M+H).

後処理

  1. temperatureby warming to room temperature
  2. stirringstirring for 1.0 hr additional
  3. customThe reaction mixture was partitioned between EtOAc/saturated sodium bicarbonate solution upon which an emulsion
  4. customformed
  5. filtrationBoth layers were filtered over a plug of Celite®
  6. washThe organic layer was washed with brine solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue was purified with FCC
  10. washeluting with ethyl acetate/heptane (0-100%)

出典と根拠

ORDレコード
ord-771b694547de44d6ab8727e1863f16e4
出典データセット
uspto-grants-2015_06
特許番号
US09056874B2

反応ノート

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