Acetone → HCID 178514769、化合物

HRID 839005ノート

反応式

HRID 839005 の反応式
[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]

参加物

6

反応物 4

HCID 180Acetone2 回HCID 962WaterHCID 516892Sodium Bicarbonate2 回HCID 178508099HCID 178508099、化合物

生成物 1

HCID 178514769HCID 178514769、化合物

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-78c1efc597ec424584b085c1dba65c90
出典データセット
uspto-grants-1978_06
特許番号
US04093723

反応ノート

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