Sodium hydride → HCID 67435148, 화합물

HRID 230710

반응식

HRID 230710 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 67435148HCID 67435148, 화합물수율 11.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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 crystallisation 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]+

후처리

  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 crystallisation from ethyl acetate-petroleum ether (40-60)

출처 및 근거

ORD 기록
ord-32173633450645a88c95458621e01b51
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566778B2

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