Acetone → HCID 178514769, 화합물

HRID 2071814노트

반응식

HRID 2071814 반응식
[C:1](=[O:4])(O)[O-].[Na+].[CH3:6][C:7]([CH3:9])=O.[OH2:10].[NH2:11][CH:12]1[C:35](=[O:36])[N:14]2[C:15]([C:32]([OH:34])=[O:33])=[C:16]([CH:19]([S:26][C:27]3[NH:31][N:30]=[N:29][N:28]=3)[CH2:20][CH2:21][S:22](=[O:25])(=[O:24])[NH2:23])[CH2:17][S:18][C@H:13]12>C(OCC)(=O)C>[C:1]([NH:11][CH:12]1[C:35](=[O:36])[N:14]2[C:15]([C:32]([OH:34])=[O:33])=[C:16]([CH:19]([S:26][C:27]3[NH:28][N:29]=[N:30][N:31]=3)[CH2:20][CH2:21][S:22](=[O:24])(=[O:25])[NH2:23])[CH2:17][S:18][C@H:13]12)(=[O:4])[C@@H:6]([C:7]1[CH:9]=[CH:17][CH:16]=[CH:15][CH:32]=1)[OH:10]

참가 물질

6

반응물 4

HCID 180Acetone2회HCID 962WaterHCID 516892Sodium Bicarbonate2회HCID 178508099HCID 178508099, 화합물

생성물 1

HCID 178514769HCID 178514769, 화합물

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 1.26 g. (15 mmol.) of sodium bicarbonate in 75 ml. of acetone and 50 ml. of water at 5° was added 2.1 g. (5 mmol.) of 7-amino-3-[1-(2-sulfamoylethyl)tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid. The solution was cooled to -10° and a solution of 1.55 g. (5.5 mmol.) of D-O-dichloroacetylmandeloyl chloride in 25 ml. of acetone was added. The reaction mixture was stirred for 30 minutes in the cold while maintaining the pH at 7.2 by addition of aqueous sodium bicarbonate, then for 1.5 hours at 25°. The mixture was extracted with ether and the aqueous phase was brought to pH 9.3 with 5% sodium carbonate and stirred for 1.5 hours at 25°. The aqueous mixture was extracted with ether, the pH adjusted to 4.5 and the solution was again extracted with ether. The aqueous phase was acidified to pH 1.5 with dilute hydrochloric acid and it was extracted with ethyl acetate. Evaporation of the extract to dryness gave a solid which was suspended in ethyl acetate and filtered. The filtrate was diluted with ether and petroleum ether to precipitate the title compound.

후처리

  1. temperatureThe solution was cooled to -10°
  2. temperaturewhile maintaining the pH at 7.2
  3. waitfor 1.5 hours at 25°
  4. extractionThe mixture was extracted with ether
  5. stirringstirred for 1.5 hours at 25°
  6. extractionThe aqueous mixture was extracted with ether
  7. extractionthe solution was again extracted with ether
  8. extractionwas extracted with ethyl acetate
  9. customEvaporation of the
  10. extractionextract to dryness
  11. customgave a solid which
  12. filtrationfiltered
  13. additionThe filtrate was diluted with ether and petroleum ether
  14. customto precipitate the title compound

출처 및 근거

ORD 기록
ord-621faeaf1b304e85be665ae34b889101
출처 데이터셋
uspto-grants-1977_09
특허 번호
US04048311

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