Sodium hydride → ethyl 7-(11-oxodibenzo[b,f][1,4]thiazepin-10(11H)-yl)heptanoate

HRID 1946626ノート

反応式

HRID 1946626 の反応式
[CH:1]1[C:6]2[C:7](=[O:16])[NH:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[S:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>CN(C=O)C>[O:16]=[C:7]1[C:6]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[S:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[N:8]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 122490Ethyl 7-bromoheptanoateHCID 374829Dibenzothiazepinone

生成物 1

HCID 58522502ethyl 7-(11-oxodibenzo[b,f][1,4]thiazepin-10(11H)-yl)heptanoate収率 69.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

Title compound 409 (0.403 g, 1.77 mmol) was dissolved in DMF (5.0 mL) and sodium hydride (60% in oil, 0.0.086 g, 2.13 mmol) was added. The reaction mixture was stirred at 50° C. for 30 minutes. Ethyl 7-bromoheptanoate (0.631 g, 2.66 mmol) was added and the reaction mixture was stirred at 50° C. for 16 hours. The mixture was cooled down to room temperature and quenched with water. The aqueous layer was extrated 3 times with at mixture of 75% ethyl acetate in hexanes. The combined organic extracts were washed with water and brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by flash chromatography (30% ethyl acetate in hexanes) to afford title compound 410 (470 mg, 69%). MS (m/z): 384.4 (M+H).

後処理

  1. stirringthe reaction mixture was stirred at 50° C. for 16 hours
  2. temperatureThe mixture was cooled down to room temperature
  3. customquenched with water
  4. additionwith at mixture of 75% ethyl acetate in hexanes
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash chromatography (30% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-01ce9a6799b840d4b8a91e51c9aa4276
出典データセット
uspto-grants-2013_03
特許番号
US08399452B2

反応ノート

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