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(+/-)-tert-Butyl 4-((tert-butylsulfinylimino)(5-cyanobenzo[d]oxazol-2-yl)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate → tert-butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-1-(1,1-dimethylethylsulfinamido)ethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

HRID 2174086
ノート
印刷プレビュー

反応式

HRID 2174086 の反応式
[C:1]([S:5]([N:7]=[C:8]([C:28]1[O:29][C:30]2[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][C:31]=2[N:32]=1)[C:9]1[C:17]([O:18][CH3:19])=[CH:16][C:15]([CH3:20])=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:6])([CH3:4])([CH3:3])[CH3:2].[CH3:39][Mg]Cl>C1COCC1.[NH4+].[Cl-].CCOC(C)=O>[C:37]([C:34]1[CH:35]=[CH:36][C:30]2[O:29][C:28]([C:8]([C:9]3[C:17]([O:18][CH3:19])=[CH:16][C:15]([CH3:20])=[C:14]4[C:10]=3[CH:11]=[CH:12][N:13]4[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])([NH:7][S:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[O:6])[CH3:39])=[N:32][C:31]=2[CH:33]=1)#[N:38]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 86701721(+/-)-tert-Butyl 4-((tert-butylsulfinylimino)(5-cyanobenzo[d]oxazol-2-yl)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylateHCID 178418332HCID 178418332、化合物

生成物 1

HCID 86701723tert-butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-1-(1,1-dimethylethylsulfinamido)ethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒
HCID 8857
Ethyl Acetate
溶媒
HCID 25517Ammonium Chloride溶媒

実験手順

To a solution of tert-butyl 4-((tert-butylsulfinyl)imino)(5-cyanobenzo[d]oxazol-2-yl)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 130-A) (0.56 g, 1.047 mmol) in THF (10.47 mL), MeMgCl (3M in THF, 1.047 mL, 3.14 mmol) was added at 0° C. After 10 minutes the mixture was diluted with sat. aq. NH4Cl and EtOAc. The aqueous layer was extracted with EtOAc, and the organic extract was dried over MgSO4, filtered and concentrated. The product was purified by flash chromatography (0-100% EtOAc:Heptanes) to provide the title compound. MS (ESI+) m/z 551.2 (M+H).

後処理

  1. extractionThe aqueous layer was extracted with EtOAc
  2. extractionthe organic extract
  3. dry with materialwas dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by flash chromatography (0-100% EtOAc:Heptanes)

出典と根拠

ORDレコード
ord-2f9d76771c6c4df0be6741a3ab789903
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09056874B2

反応ノート

読み込み中…

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