Sodium hydride → (S)-2,3,10,10a-tetrahydro-1H,5H-pyrrolo[2,1-c]thieno[2,3-f][1,4]oxazepine-5-one

HRID 1392894

反応式

HRID 1392894 の反応式
Cl[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7](O)=O.C(N1C=CN=C1)(N1C=CN=C1)=[O:11].[NH:22]1[CH2:26][CH2:25][CH2:24][C@H:23]1[CH2:27][OH:28].[H-].[Na+]>CN(C)C=O.O>[S:4]1[CH:3]2[CH2:7][N:22]3[CH:26]=[CH:25][CH:24]=[C:23]3[C:27](=[O:11])[O:28][C@H:2]2[CH2:6][CH2:5]1

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 640091L-ProlinolHCID 7012693-Chlorothiophene-2-carboxylic acid

生成物 1

HCID 67435148(S)-2,3,10,10a-tetrahydro-1H,5H-pyrrolo[2,1-c]thieno[2,3-f][1,4]oxazepine-5-one収率 11.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-chlorothiophene-2-carboxylic acid (0.5 g; 6.325 mmol) in dimethylformamide (5 ml) was added 1,1′-carbonyldiimidazole (1.07 g; 6.64 mmol) and the solution stirred at room temperature for 1 h, followed by the addition of (S)-(+)-2-pyrrolidinemethanol (0.655 ml; 6.64 mmol). The reaction was stirred at room temperature overnight whereupon 60% sodium hydride in mineral oil (0.507 g; 12.7 mmol) was carefully added and the mixture was heated slowly to 150° C. with the progress of the reaction being monitored by thin layer chromatography. The reaction was cautiously diluted with water and extracted with ethyl acetate and the organic layer washed with water then dried (Na2SO4) and evaporated to give the crude product. Purification by flash chromatography eluting with 0-10% (v/v) methanol in dichloromethane followed by crystalisation from ethyl acetate-petroleum ether (40-60) afforded the title compound (0.15 g). M.p.: 167-167.5° C.; EIMS: m/z=222.2 [M+H]+

後処理

  1. additionwas carefully added
  2. temperaturethe mixture was heated slowly to 150° C. with the progress of the reaction
  3. extractionextracted with ethyl acetate
  4. washthe organic layer washed with water
  5. dry with materialthen dried (Na2SO4)
  6. customevaporated
  7. customto give the crude product
  8. customPurification by flash chromatography
  9. washeluting with 0-10% (v/v) methanol in dichloromethane
  10. customfollowed by crystalisation from ethyl acetate-petroleum ether (40-60)

出典と根拠

ORDレコード
ord-1da528887de840a48b3bca6b4b4628df
出典データセット
uspto-grants-2008_03
特許番号
US07345036B2

関連ノート

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